CN111099986B - 氢化反应方法 - Google Patents

氢化反应方法 Download PDF

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CN111099986B
CN111099986B CN201911285045.7A CN201911285045A CN111099986B CN 111099986 B CN111099986 B CN 111099986B CN 201911285045 A CN201911285045 A CN 201911285045A CN 111099986 B CN111099986 B CN 111099986B
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CN111099986A (zh
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崔秀灵
王勇
皮超
吴养洁
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Zhengzhou University
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Abstract

本发明涉及一种氢化反应方法，属于有机合成技术领域。本发明的氢化反应方法，包括以下步骤：氢受体化合物、频哪醇硼烷、催化剂在质子氢存在的条件下于溶剂中进行氢转移反应，使得氢受体化合物进行氢化反应；所述催化剂为钯催化剂、铱催化剂、铑催化剂中的一种或两种以上；所述氢受体化合物包含碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧中的一种或两种以上的官能团。本发明的方法反应条件温和，易操作，收率高，反应时间短，底物适用范围广，适应于碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧官能团，具有较好的选择性，反应专一性强。

Description

氢化反应方法
技术领域
本发明涉及一种氢化反应方法，属于有机合成技术领域。
背景技术
氢化反应指氢分子加成到有机化合物的不饱和基团上的反应，催化转移氢化反应catalytic transfer hydrogenation，是指在催化剂的作用下，氢由氢的给体转移到有机化合物反应底物的反应。
不饱和化合物的氢化反应是有机合成中应用广泛且具有重要研究意义和实用价值的反应，在天然产物、医药及其中间体等有机化合物合成中均具有重要的应用价值。现有的大多数氢化反应仅适应于某一种不饱和键，适应范围较窄，不利于氢化反应的推广应用。
发明内容
本发明的目的在于提供一种氢化反应方法，该氢化反应方法的适应范围广，适应于碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧官能团的氢化反应。
本发明的技术方案如下：
一种氢化反应方法，包括以下步骤：氢受体化合物、频哪醇硼烷、催化剂在质子氢存在的条件下于溶剂中进行氢转移反应，使得氢受体化合物进行氢化反应；所述催化剂为钯催化剂、铱催化剂、铑催化剂中的一种或两种以上；所述氢受体化合物包含碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧中的一种或两种以上的官能团。
本发明的氢化反应方法中，氢受体化合物、频哪醇硼烷、催化剂在质子氢存在的条件下于溶剂中即可进行氢转移反应，使得氢受体化合物进行氢化反应。本发明的方法反应条件温和，易操作，收率高，反应时间短，底物适用范围广，适应于碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧官能团，具有较好的选择性，反应专一性强，后处理简便且绿色。
本发明的方法可以较好选择性优先还原一种不饱和键(视不饱和键的活性而定)，而另一种不饱和键得以保留；当底物中含有多种不饱和键时，可以较好选择性优先还原一种或多种不饱和键，而其它不饱和键得以保留。比如，对于同时含双键和酰胺键的氢受体化合物，可以选择性地优先使得双键进行氢化反应的同时保留酰胺键，比如，可从同时含羰基、双键的氢受体化合物选择性地对双键进行氢化；可从同时含酯基、双键的氢受体化合物选择性地对双键进行氢化；可从同时含氰基、双键的氢受体化合物选择性地对双键进行氢化；可从同时含硝基、双键的氢受体化合物选择性地对双键进行氢化；可从同时含醛基、硝基的氢受体化合物选择性地对醛基进行氢化；可从同时含羰基、氰的氢受体化合物选择性地对羰基进行氢化；可从同时含硝基、羰基的氢受体化合物选择性地对硝基进行氢化。
当反应底物中包含两种或两种以上不饱和键时，可以选择性还原一种或者部分不饱和键，剩余不饱和键得以保留。当反应底物中包含两种或两种以上不饱和键时，可以同时完全还原所有不饱和键。
可以理解的是，“所述氢受体化合物包含碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧中的一种或两种以上的官能团”指的是，氢受体化合物可以只含有碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧中的一种官能团，氢受体化合物也可以是含有碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧中的两种官能团，比如，含碳碳双键和硝基的氢受体化合物，含碳氧双键和碳氮三键的氢受体化合物，含两个碳碳双键的氢受体化合物，氢受体化合物也可以是含有碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、硝基、碳氮三键、环氧中的三种官能团，不再一一举例。
优选地，所述氢受体化合物自身含质子氢，所述质子氢由氢受体化合物自身提供、和/或通过通入氢气提供、和/或通过质子性溶剂提供；或者，所述氢受体化合物自身不含质子氢，所述质子氢通过通入氢气提供、和/或通过质子性溶剂提供。
优选地，所述质子氢由羧酸、醇、酚、胺、酰胺、水、氢气中的一种或两种以上提供。可以理解的是，当质子氢由水或氢气提供时，直接向溶剂中加入水或通入氢气即可，当质子氢由羧酸、醇、酚、胺、酰胺提供时，羧酸、醇、酚、胺、酰胺可以为氢受体化合物本身，也可以是相应的质子性溶剂，比如，质子氢由羧酸提供时，含有羧基的氢受体化合物本身可以作为质子供体，同时，还可以再外加如质子性溶剂，或者，将羧酸类的质子性溶剂作为质子供体，如乙酸。
优选地，所述氢受体化合物选自式Ⅰ～式Ⅸ所示的化合物、环烯烃、杂环烯烃、稠环烯烃，或为式Ⅰ～式Ⅸ、环烯烃、杂环烯烃、稠环烯烃中的两种或两种以上拼接形成的拼接化合物；
Figure BDA0002317747700000031
式中，n为1～3的整数；
R1～R4各自独立地选自氢、芳基、R21取代芳基、烷基、R21取代烷基、环烷基、杂环烷基、R21取代环烷基；
R5、R6、R10、R17～R20各自独立地选自氢、芳基、R21取代芳基、烷基、R21取代烷基、环烷基、杂环烷基、R21取代环烷基；
R7～R9、R11～R16各自独立地选自芳基、R21取代芳基、烷基、R21取代烷基、环烷基、杂环烷基、R21取代环烷基；
其中，所述R21选自苯、R22取代苯、C1～C4烷基、R22取代C1～C4烷基、C1～C4烷氧基、R22取代C1～C4烷氧基、卤素、氰、硝基、氨基、亚氨基、羟基、羧基中的一种或两种以上，所述R22选自卤素、氰、硝基、氨基、羟基、羧基中的一种或两种以上；
且R1～R22中的两个或多个取代基可以相连形成环。
Figure BDA0002317747700000032
经氢化反应，碳碳双键转变为单键，可形成
Figure BDA0002317747700000033
Figure BDA0002317747700000034
经氢化反应，碳碳三键可转变为双键，如
Figure BDA0002317747700000035
或
Figure BDA0002317747700000036
也可转变为单键，如
Figure BDA0002317747700000037
Figure BDA0002317747700000038
经氢化反应，醛基可转变为
Figure BDA0002317747700000039
Figure BDA00023177477000000310
经氢化反应，碳氮双键加氢可转变为
Figure BDA00023177477000000311
Figure BDA0002317747700000041
经氢化反应，氮氮双键加氢可转变为
Figure BDA0002317747700000042
Figure BDA0002317747700000043
经氢化反应，硝基加氢形成氨基，如R13-NH2。
Figure BDA0002317747700000044
经氢化反应，碳氧双键加氢可转变为
Figure BDA0002317747700000045
此处的碳氧双键为羰基。
Figure BDA0002317747700000046
经氢化反应，氰加氢可转变为
Figure BDA0002317747700000047
Figure BDA0002317747700000048
经氢化反应，环氧加氢开环可转变为
Figure BDA0002317747700000049
优选地，所述氢受体化合物的结构式如下所示：
Figure BDA00023177477000000410
Figure BDA0002317747700000051
为了进一步提高催化效率，优选地，所述催化剂为醋酸钯、氯化钯、三氟乙酸钯、氯化铱、氯化铑、二氯(五甲基环戊二烯基)合铱(III)、二氯(五甲基环戊二烯基)合铑(III)中的一种或两种以上。
该方法的反应条件比较温和，优选地，所述氢转移反应的反应温度为5～40℃。
该反应在室温下(25℃)即可进行反应。
优选地，所述氢转移反应的反应时间为6～18小时。
为了进一步提高氢转移反应的效率，优选地，所述氢受体化合物与频哪醇硼烷的摩尔比为1:(1～3.3)。
为了进一步提高氢转移反应的效率，优选地，所述氢受体化合物与质子供体的摩尔比为1：(1～110)。
为了进一步提高氢转移反应的效率，优选地，所述氢受体化合物与催化剂的摩尔比为100:(0.1～10)。
优选地，所述溶剂为二氯甲烷、乙酸乙酯、三氯甲烷、甲醇、乙醇、1，2-二氯乙烷、甲苯、四氢呋喃、乙醚、乙腈、1，4-二氧六环、叔丁基甲基醚、丙酮、水中的一种或两种以上的混合。当氢受体化合物本身含有羧基、羟基、氨基、酰胺时，可以不额外加质子性溶剂，此时的溶剂可以是非质子性溶剂，也可以是质子性溶剂，或者非质子性溶剂与质子性溶剂的混合，当氢受体化合物不能作为质子供体时，需要额外加入质子性溶剂，此时的溶剂可以是质子性溶剂，也可以是质子性溶剂与非质子性溶剂的混合。
所述氢转移反应完成后，还包括浓缩及柱层析纯化的步骤。
具体实施方式
下面结合具体实施方式对本发明作进一步说明。
本发明的实施例中，质子供体和频哪醇硼烷与氢受体化合物进行氢转移反应，氢受体化合物接受氢，质子供体和频哪醇硼烷(简称HBPin)提供氢，比如，质子性溶剂为R31OH时，质子供体和频哪醇硼烷失去氢后形成R31OBPin，质子性溶剂为R32R33NH时，质子供体和频哪醇硼烷失去氢后形成R32R33NBPin。
一、本发明的氢化反应方法的具体实施例如下：
实施例1
氢化肉硅酸的制备，氢化反应的反应式如下式所示：
Figure BDA0002317747700000061
式ⅰ所示的肉桂酸、频哪醇硼烷、醋酸钯催化剂在二氯甲烷溶剂中反应生成式ⅱ所示的化合物，式ⅱ所示的化合物在后处理过程中与水接触，生成式ⅲ所示的化合物。具体步骤如下所示：
将史莱克管中的气体环境置换为氮气环境，加入肉桂酸0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液用10mL乙酸乙酯稀释，加入饱和碳酸氢钠10mL，乙酸乙酯萃取三次，用浓盐酸将水相pH值调至酸性，再用乙酸乙酯萃取，取有机相真空下浓缩，以93％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:10.38(br,s,1H),7.32-7.26(m,2H),7.24-7.27(m,3H),2.96(t,J＝7.6Hz,2H),2.68(t,J＝7.5Hz,2H)；13C NMR(CDCl3)δ:179.3,140.1,128.5,128.2,126.4,35.6,30.5.
实施例2
4-氟氢化肉桂酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000071
将史莱克管中的气体环境置换为氮气环境，加入4-氟肉桂酸0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液用10mL乙酸乙酯稀释，加入饱和碳酸氢钠10mL，乙酸乙酯萃取三次，用浓盐酸将水相pH值调至酸性，再用乙酸乙酯萃取，取有机相真空下浓缩，以>99％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:11.1(br,s,1H),7.20-7.13(m,2H),7.01-6.93(m,2H),2.93(t,J＝7.6Hz,2H),2.66(t,J＝6.5Hz,2H)；13C NMR(CDCl3)δ:178.3,161.5(d,JC-F＝244.3Hz),135.7(d,JC-F＝3.3Hz),129.7(d,JC-F＝7.8Hz),115.3(d,JC-F＝21.2Hz),35.6,29.7；19F NMR(CDCl3)δ:-116.8.
实施例3
3-三氟甲基氢化肉桂酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000072
将史莱克管中的气体环境置换为氮气环境，加入3-三氟甲基肉桂酸0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液用10mL乙酸乙酯稀释，加入饱和碳酸氢钠10mL，乙酸乙酯萃取三次，用浓盐酸将水相pH值调至酸性，再用乙酸乙酯萃取，取有机相真空下浓缩，以97％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:10.66(br,s,1H),7.51-7.45(m,2H),7.45-7.37(m,2H),3.02(t,J＝7.6Hz,2H),2.72(t,J＝7.7Hz,2H)；13CNMR(CDCl3)δ:178.8,141.1,130.8,130.9(q,JC-F＝32.1Hz),129.0,124.2(q,JC-F＝272.2Hz),125.1(q,JC-F＝3.9Hz),123.3(q,JC-F＝3.8Hz),35.3,30.3；19F NMR(CDCl3)δ:-62.6.
实施例4
4-羟基氢化肉桂酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000073
将史莱克管中的气体环境置换为氮气环境，加入4-羟基肉桂酸0.25mmol，醋酸钯0.0025mmol，乙酸乙酯0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液用10mL乙酸乙酯稀释，加入饱和碳酸氢钠10mL，乙酸乙酯萃取三次，用浓盐酸将水相pH值调至酸性，再用乙酸乙酯萃取，取有机相真空下浓缩，以>99％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(d6-DMSO)δ:12.06(br,s,1H),9.15(s,1H),7.00(d,J＝8.4Hz,2H),6.65(d,J＝8.4Hz,2H),2.69(t,J＝7.6Hz,2H),2.45(t,J＝7.8Hz,2H)；13C NMR(d6-DMSO)δ:174.4,156.0,131.4,129.5,115.5,36.2,30.0.
实施例5
2-甲基-3-苯基丙酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000081
将史莱克管中的气体环境置换为氮气环境，加入2-甲基-3-苯基丙烯酸0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液用10mL乙酸乙酯稀释，加入饱和碳酸氢钠10mL，乙酸乙酯萃取三次，用浓盐酸将水相pH值调至酸性，再用乙酸乙酯萃取，取有机相真空下浓缩，以99％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:10.35(br,s,1H),7.31-7.26(m,2H),7.24-7.20(m,1H),7.20-7.15(m,2H),3.08(dd,J＝13.4,6.3Hz,1H),2.82-2.71(m,1H),2.66(dd,J＝13.3,8.0Hz,1H),1.17(d,J＝6.7Hz,3H)；13C NMR(CDCl3)δ:182.6,139.0,129.0,128.4,126.4,41.2,39.2,16.4.
实施例6
4-乙基苯甲酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000082
将史莱克管中的气体环境置换为氮气环境，加入4-乙烯基苯甲酸0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液用10mL乙酸乙酯稀释，加入饱和碳酸氢钠10mL，乙酸乙酯萃取三次，用浓盐酸将水相pH值调至酸性，再用乙酸乙酯萃取，取有机相真空下浓缩，以>99％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:12.34(br,s,1H),8.04(d,J＝8.2Hz,2H),7.30(d,J＝8.1Hz,2H),2.72(q,J＝7.6Hz,2H),1.27(t,J＝7.6Hz)；13C NMR(CDCl3)δ:172.6,150.8,130.4,128.0,126.8,29.0,15.2.
实施例7
双环[2.2.1]庚烷-2-羧酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000091
将史莱克管中的气体环境置换为氮气环境，加入5-降冰片烯-2-羧酸0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以>99％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:11.23(br,s,1H,endo and exo),2.85-2.76(m,1H,endo),2.60(s,1H,endo),2.56(d,J＝2.6Hz,0.34H,exo),2.36(dd,J＝8.9,5.4Hz,0.34H,exo),2.33-2.21(m,1.34H,endo and exo),1.89-1.80(m,0.34H,exo),1.74-1.14(m,11H,endo and exo)；13C NMR(CDCl3)δ:181.5,46.0,40.5,40.2,37.0,31.7,29.1,24.8(endo)；182.5,46.4,40.9,36.5,36.0,34.0,29.4,28.6(exo).
实施例8
环戊基甲酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000092
将史莱克管中的气体环境置换为氮气环境，加入3-环戊烯甲酸0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以>99％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:10.69(br,s,1H),2.77(quint,J＝8.1Hz,1H),1.98-1.78(m,4H),1.78-1.65(m,2H),1.64-1.53(m,2H)；13C NMR(CDCl3)δ:183.2,43.6,29.9,25.8.
实施例9
苯丙醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000093
将史莱克管中的气体环境置换为氮气环境，加入肉桂醇0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以90％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.30-7.23(m,2H),7.22-7.12(m,3H),3.63(t,J＝6.4Hz,2H),2.68(t,J＝7.9Hz,2H),2.03(br,s,1H),1.91-1.81(m,2H)；13C NMR(CDCl3)δ:141.8,128.3,128.3,125.8,62.0,34.1,32.0.
实施例10
1-苯丙醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000101
将史莱克管中的气体环境置换为氮气环境，加入3-苯基丙烯-3-醇0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以78％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.37-7.31(m,4H),7.30-7.23(m,1H),4.58(t,J＝6.6Hz,1H),2.02(br,s,1H),1.88-1.67(m,2H),0.91(t,J＝7.4Hz,3H)；13C NMR(CDCl3)δ:144.5,128.3,127.4,125.9,76.0,31.8,10.1.
实施例11
2-苯基-2-戊醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000102
将史莱克管中的气体环境置换为氮气环境，加入2-苯基-4-戊烯-2-醇0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以88％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.46-7.40(m,1H),7.33(t,J＝7.4Hz,2H),7.23(tt,J＝7.3,1.2Hz,1H),1.85-1.73(m,2H),1.71(br,s,1H),1.55(s,3H),1.34-1.24(m,1H),1.22-1.08(m,1H),0.86(t,J＝7.3Hz,3H)；13C NMR(CDCl3)δ:148.1,128.1,126.4,124.7,74.7,46.5,30.1,17.3,14.4.
实施例12
二环[2.2.1]庚-2-醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000103
将史莱克管中的气体环境置换为氮气环境，加入5-降冰片烯-2-甲醇0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以>99％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:4.27-4.19(m,1H,endo),3,76(d,J＝6.8Hz,0.15H,exo),2.29-2.22(m,1.15H,endo and exo),2.20-2.12(m,1.15H,endo and exo),2.02-1.83(m,2.15H,endo and exo),1.70-1.23(m,8H,endo and exo),1.15-1.09(m,0.15H,exo),1.06-0.97(m,0.30H,exo),0.84(dt,J＝12.9,3.4Hz,1.15H,endo and exo)；13C NMR(CDCl3)δ:(endo)73.1,42.5,39.6,37.6,37.2,29.8,19.9；(exo)75.0,44.3,42.4,35.4,34.4,28.1,24.4.
实施例13
3,7,11-三甲基-6,10-十二烷二烯-3-醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000111
将史莱克管中的气体环境置换为氮气环境，加入3,7,11-三甲基-1,6,10-十二烷三烯-3-醇0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以>99％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:5.18-5.03(m,2H),2.11-1.95(m,6H),1.71-1.57(m,9H),1.54-1.43(m,4H),1.57and 1.52(s,3H),0.93-0.86(m,3H)；13C NMR(CDCl3)δ:(trans)135.26,131.57,125.20,125.20,72.89,41.39,34.27,31.90,26.55,25.71,23.36,22.36,17.61,8.20；(cis)135.26,131.38,124.39,124.25,72.94,41.04,39.69,34.29,26.65,26.25,25.67,22.52,17.66,15.94,8.22.
实施例14
2-丙基苯酚的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000112
将史莱克管中的气体环境置换为氮气环境，加入2-烯丙基苯酚0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以92％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.11(dd,J＝7.4,1.3Hz,1H),7.07(td,J＝7.6,1.6Hz,1H),6.86(td,J＝7.4,1.0Hz,1H),6.75(dd,J＝8.0,0.8Hz,1H),4.7(s,1H),2.57(t,J＝7.5Hz,2H),1.70-1.59(m,2H),0.97(t,J＝7.3Hz,3H)；13C NMR(CDCl3)δ:153.4,130.2,128.3,127.0,120.7,115.2,31.9,22.9,14.0.
实施例15
N-丙基苯胺的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000121
将史莱克管中的气体环境置换为氮气环境，加入N-烯丙基苯胺0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以57％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.19-7.13(m,2H),6.68(tt,J＝7.3,1.0Hz,1H),6.60(dd,J＝8.6,1.0Hz,2H),3.63(br,s,1H),3.08(t,J＝7.1Hz,2H),1.69-1.57(m,2H),0.99(t,J＝7.4Hz,3H)；13C NMR(CDCl3)δ:148.5,129.2,117.1,112.7,45.8,22.7,11.6.
实施例16
3-苯基丙酰胺的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000122
将史莱克管中的气体环境置换为氮气环境，加入肉桂酰胺0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以99％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.33-7.27(m,2H),7.24-7.17(m,3H),5.54(br,s,1H),5.37(br,s,1H),2.97(t,J＝7.6Hz,2H),2.53(t,J＝8.0Hz,2H)；13C NMR(CDCl3)δ:174.4,140.6,128.6,128.3,126.3,37.5,31.4.
实施例17
丁二酰亚胺的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000123
将史莱克管中的气体环境置换为氮气环境，加入马来酰亚胺0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以66％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:8.48(br,s,1H),2.77(s,4H)；13C NMR(CDCl3)δ:177.5,29.5.
实施例18
3-苯基丙酸甲酯的制备，氢化反应的反应式如下式所示：
Figure BDA0002317747700000131
将史莱克管中的气体环境置换为氮气环境，加入肉桂酸甲酯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以96％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.32-7.25(m,1H),7.23-7.17(m,3H),3.67(s,3H),2.95(t,J＝7.6Hz,2H),2.63(t,J＝8.2Hz,2H)；13C NMR(CDCl3)δ:173.3,140.5,128.5,128.2,126.2,51.5,35.6,30.9.
实施例19
丙酸苯酯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000132
将史莱克管中的气体环境置换为氮气环境，加入丙烯酸苯酯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以88％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.37(t,J＝8.3Hz,2H),7.22(t,J＝7.4Hz,1H),7.08(d,J＝8.4Hz,2H),2.59(q,J＝7.6Hz,2H),1.26(t,J＝7.5Hz)；13C NMR(CDCl3)δ:172.9,150.7,129.3,125.7,121.5,27.7,9.0.
实施例20
3-苯基丙酸苄酯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000133
将史莱克管中的气体环境置换为氮气环境，加入肉桂酸苄酯0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以89％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.38-7.14(m,10H),5.10(s,1H),2.96(t,J＝7.6Hz,2H),2.68(t,J＝7.5Hz,2H)；13C NMR(CDCl3)δ:172.7,140.4,135.9,128.5,128.5,128.3,128.2,128.2,126.2,66.2,35.8,30.9.
实施例21
3-苯基丙腈的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000141
将史莱克管中的气体环境置换为氮气环境，加入肉桂腈0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以84％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.37-7.31(m,2H),7.30-7.25(m,1H),7.25-7.19(m,2H),2.95(t,J＝7.4Hz,2H),2.61(t,J＝7.4Hz,2H)；13C NMR(CDCl3)δ:138.0,128.8,128.2,127.2,119.1,31.5,19.3.
实施例22
3-苯基苄基酮的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000142
将史莱克管中的气体环境置换为氮气环境，加入查尔酮0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，甲醇0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以76％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.95(d,J＝7.2Hz,2H),7.54(t,J＝7.4Hz,1H),7.44(t,J＝7.8Hz,2H),7.33-7.23(m,4H),7.20(t,J＝7.0Hz,1H),3.30(t,J＝8.1Hz,2H),3.07(t,J＝8.0Hz,2H)；13C NMR(CDCl3)δ:199.2,141.2,136.8,133.0,128.6,128.5,128.4,128.0,126.1,40.4,30.1.
实施例23
1,2-二苯基乙烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000143
将史莱克管中的气体环境置换为氮气环境，加入顺式1,2-二苯基乙烯0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，甲醇0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以97％收率得到的目标产物为白色固体；或者，将史莱克管中的气体环境置换为氮气环境，加入反式1,2-二苯基乙烯0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以93％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.30-7.23(m,4H),7.21-7.14(m,6H),2.91(s,4H)；13C NMR(CDCl3)δ:141.7,128.4,128.3,125.9,37.9.
实施例24
1,1-二苯基乙烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000151
将史莱克管中的气体环境置换为氮气环境，加入1,1-二苯基乙烯0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以93％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.30-7.24(m,4H),7.23-7.20(m,4H),7.17(tt,J＝7.1,1.4Hz,2H),4.14(q,J＝7.2Hz,1H),1.63(d,J＝7.2Hz,3H)；13C NMR(CDCl3)δ:146.3,128.3,127.6,126.0,44.7,21.8.
实施例25
乙基苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000152
将史莱克管中的气体环境置换为氮气环境，加入苯乙烯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率为>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.31-7.16(m,2H),7.22-7.14(m,3H),2.65(q,J＝7.6Hz,2H),1.24(t,J＝7.6Hz,3H)；13C NMR(CDCl3)δ:144.2,128.3,127.8,125.6,28.9,15.6.
实施例26
1-乙基-4-氟苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000153
将史莱克管中的气体环境置换为氮气环境，加入4-氟苯乙烯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率为>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.17-7.11(m,2H),6.96(tt,J＝8.8,2.1Hz,2H),2.62(q,J＝7.6Hz,2H),1.22(t,J＝7.6Hz,3H)；13C NMR(CDCl3)δ:161.1(d,JC-F＝242.8Hz),139.8(d,JC-F＝3.5Hz),129.1(d,JC-F＝7.8Hz),114.9(d,JC-F＝21.1Hz),28.1,15.8；19F NMR(CDCl3)δ:-118.3.
实施例27
1-溴-4-乙基苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000161
将史莱克管中的气体环境置换为氮气环境，加入4-溴苯乙烯0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，甲醇2.75mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率为>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.39(tt,J＝8.4,1.8Hz,2H),7.07(d,J＝8.4Hz,2H),2.60(q,J＝7.6Hz,2H),1.21(t,J＝7.6Hz,3H)；13C NMR(CDCl3)δ:143.1,131.3,129.6,119.2,28.3,15.5.
实施例28
1-溴-2-乙基苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000162
将史莱克管中的气体环境置换为氮气环境，加入2-溴苯乙烯0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，甲醇2.75mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率为>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.52(d,J＝7.8Hz,1H),7.25-7.20(m,2H),7.08-6.99(m,1H),2.76(q,J＝7.6Hz,2H),1.23(t,J＝7.6Hz,3H)；13C NMR(CDCl3)δ:143.3,132.7,129.5,127.5,127.3,124.3,29.4,14.2.
实施例29
1-溴-3-乙基苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000163
将史莱克管中的气体环境置换为氮气环境，加入3-溴苯乙烯0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，甲醇2.75mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率为>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.34(s,1H),7.30(dt,J＝7.2,1.8Hz,1H),7.17-7.09(m,2H),2.62(q,J＝7.6Hz,2H),1.22(t,J＝7.6Hz,3H)；13C NMR(CDCl3)δ:146.5,130.9,129.8,128.7,126.5,122.4,28.6,15.3.
实施例30
1-乙基-4-三氟甲基苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000171
将史莱克管中的气体环境置换为氮气环境，加入4-三氟甲基苯乙烯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率为>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.53(d,J＝8.1Hz,2H),7.39(d,J＝8.0Hz,2H),2.70(q,J＝7.6Hz,2H),1.26(t,J＝7.6Hz,3H)；13C NMR(CDCl3)δ:148.3,128.1,125.2(q,JC-F＝3.8Hz),124.4(q,JC-F＝271.5Hz),28.8,15.3；19F NMR(CDCl3)δ:-62.3.
实施例31
1-乙基-4硝基苯乙烯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000172
将史莱克管中的气体环境置换为氮气环境，加入4-硝基苯乙烯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以79％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:8.14(dt,J＝8.8,1.9Hz,2H),7.34(d,J＝8.8Hz,2H),2.76(q,J＝7.6Hz,2H),1.28(t,J＝7.6Hz,3H)；13C NMR(CDCl3)δ:152.0,146.2,128.6,123.6,28.8,15.0.
实施例32
异丙基苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000173
将史莱克管中的气体环境置换为氮气环境，加入α-甲基苯乙烯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率为>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.32-7.26(m,2H),7.25-7.21(m,2H),7.18(tt,J＝7.2,1.4Hz,1H),2.90(sept,J＝6.9Hz,1H),1.26(d,J＝6.9Hz,6H)；13C NMR(CDCl3)δ:148.8,128.3,126.4,125.7,34.1,24.0.
实施例33
叔丁基二甲基(3-苯丙氧基)硅烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000181
将史莱克管中的气体环境置换为氮气环境，加入叔丁基(肉桂氧基)二甲基硅烷0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以85％收率得到的目标产物为淡黄色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.33-7.27(m,2H),7.24-7.17(m,3H),3.67(t,J＝6.3Hz,2H),2.71(t,J＝7.6Hz,2H),1.91-1.82(m,2H),0.94(s,9H),0.08(s,6H)；13C NMR(CDCl3)δ:142.2,128.5,128.3,125.6,62.3,34.5,32.1,26.0,18.3,-5.3.
实施例34
(3-(苄氧基)丙基)苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000182
将史莱克管中的气体环境置换为氮气环境，加入肉桂氧基苄基醚0.25mmol，醋酸钯0.025mmol，二氯甲烷0.5mL，甲醇0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以89％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.37-7.33(m,4H),7.30-7.23(m,3H),7.20-7.15(m,3H),4.51(s,2H),3.49(t,J＝6.4Hz,2H),2.72(t,J＝7.9Hz,2H),1.98-1.90(m,2H)；13C NMR(CDCl3)δ:142.0,138.6,128.5,128.4,128.3,127.7,127.5,125.7,72.9,69.5,32.4,31.4.
实施例35
氢化黄体酮的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000183
将史莱克管中的气体环境置换为氮气环境，加入黄体酮0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，水2.75mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以95％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:2.69(t,J＝13.7Hz,1H,5β-4w),2.13(s,3H,5β-4w),2.12(s,1.7H,5α-4w),1.03(s,3H,5β-4w),1.02(s,1.7H,5α-4w),0.64(s,3H,5β-4w),0.63(s,1.7H,5α-4w)；13C NMR(CDCl3)δ:(5β-4w)212.81,209.20,63.58,56.44,44.11,44.02,42.13,40.55,38.93,37.00,36.81,35.36,34.76,31.38,26.36,25.60,24.24,22.74,22.47,21.04,13.29；(5α-4w)211.61,209.28,63.55,56.28,53.49,46.50,44.48,44.01,38.76,38.38,37.97,35.52,35.20,31.48,31.36,28.67,24.26,22.66,21.28,13.29,11.31.
实施例36
癸烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000191
将史莱克管中的气体环境置换为氮气环境，加入1-癸烯0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以>99％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:1.35-1.20(m,16H),0.88(t,J＝7.0Hz)；13CNMR(CDCl3)δ:32.0,29.7,29.4,22.7,14.1.
实施例37
1-叔丁氧羰基吡咯烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000192
将史莱克管中的气体环境置换为氮气环境，加入1-叔丁氧羰基吡咯0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以87％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:3.39-3.21(m,4H),1.83(br,s,4H),1.46(s,9H)；13C NMR(CDCl3)δ:154.6,78.8,45.9,45.6,25.7,24.9.
实施例38
丙基苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000193
将史莱克管中的气体环境置换为氮气环境，加入烯丙基苯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.30-7.26(m,2H),7.20-7.14(m,3H),2.59(t,J＝7.9Hz,2H),1.69-1.60(m,2H),0.94(t,J＝7.4Hz)；13C NMR(CDCl3)δ:142.7,128.4,128.2,125.6,38.1,24.6,13.8.
实施例39
环辛烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000201
将史莱克管中的气体环境置换为氮气环境，加入环辛烯0.25mmol，醋酸钯0.0125mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，核磁收率>99％，反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:1.53(s,16H)；13C NMR(CDCl3)δ:26.7.
实施例40
1-苯基-1-丁烯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000202
将史莱克管中的气体环境置换为氮气环境，加入1-苯-1,3-丁二烯0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.25mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.36-7.32(m,2H),7.31-7.26(m,2H),7.18(tt,J＝7.2,1.3Hz,1H),6.38(d,J＝15.9Hz,1H),6.27(dt,J＝15.8,6.2Hz,1H),2.28-2.18(m,2H),1.09(t,J＝7.4Hz,3H)；13C NMR(CDCl3)δ:137.9,132.6,128.8,128.5,126.7,125.9,26.0,13.6.
实施例41
1,1,2,2-四苯基乙烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000203
将史莱克管中的气体环境置换为氮气环境，加入四苯基乙烯0.25mmol，醋酸钯0.025mmol，乙酸乙酯2mL，水2.75mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以83％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.19-7.13(m,8H),7.10(t,J＝7.8Hz,8H),7.00(tt,J＝7.2,1.3Hz,4H),4.77(s,2H)；13C NMR(CDCl3)δ:143.4,128.5,128.1,125.8,56.3.
实施例42
氢化肉桂酸内酯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000204
将史莱克管中的气体环境置换为氮气环境，加入香豆素0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，甲醇0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以93％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.25(td,J＝8.1,0.7Hz,1H),7.20(d,J＝7.2Hz,1H),7.10(td,J＝7.4,1.0Hz,1H),7.04(d,J＝8.1Hz,1H),3.01(t,J＝6.8Hz,2H),2.81-2.75(m,2H)；13C NMR(CDCl3)δ:168.5,151.9,128.2,127.9,124.3,122.6,116.9,29.2,23.6.
实施例43
2,3-二氢苯并呋喃的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000211
将史莱克管中的气体环境置换为氮气环境，加入苯并呋喃0.25mmol，醋酸钯0.025mmol，二氯甲烷0.5mL，甲醇13.75mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.19(dd,J＝7.3,0.7Hz,1H),7.10(t,J＝8.0Hz,1H),6.84(td,J＝7.4,0.8Hz,1H),6.79(d,J＝8.0Hz,1H),4.55(t,J＝8.7Hz,2H),3.21(t,J＝8.7Hz,2H)；13C NMR(CDCl3)δ:160.0,127.9,126.8,124.9,120.3,109.3,71.0,29.7.
实施例44
1,2,3,4-四氢喹啉的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000212
将史莱克管中的气体环境置换为氮气环境，加入喹啉0.25mmol，醋酸钯0.02mmol，二氯甲烷0.5mL，甲醇27.5mmol，搅拌下加入频哪醇硼烷0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以92％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:6.98-6.90(m,2H),6.59(td,J＝7.3,0.9Hz,1H),6.45(d,J＝7.9Hz,1H),3.76(br,s,1H),3.28(t,J＝5.5Hz,2H),2.75(t,J＝6.4Hz,2H),1.97-1.89(m,2H)；13C NMR(CDCl3)δ:144.7,129.5,126.7,121.4,116.9,114.1,41.9,26.9,22.1.
实施例45
1,2,3,4-四氢喹喔啉的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000221
将史莱克管中的气体环境置换为氮气环境，加入喹喔啉0.25mmol，醋酸钯0.02mmol，二氯甲烷0.5mL，甲醇27.5mmol，搅拌下加入频哪醇硼烷0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以>99％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:6.57(dd,J＝5.8,3.4Hz,2H),6.48(dd,J＝5.7,3.4Hz,2H),3.59(br,s,2H),3.40(br,s,4H)；13C NMR(CDCl3)δ:133.6,118.7,114.6,41.3.
实施例46
2-苯基-5,6,7,8-四氢咪唑并[1,2-a]吡啶的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000222
将史莱克管中的气体环境置换为氮气环境，加入2-苯基咪唑并[1,2-a]吡啶0.25mmol，醋酸钯0.025mmol，二氯甲烷2mL，甲醇27.5mmol，搅拌下加入频哪醇硼烷0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以86％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.73(d,J＝7.8Hz,2H),7.34(t,J＝7.6Hz,2H),7.20(t,J＝7.4Hz,1H),7.05(s,1H),3.95(t,J＝5.5Hz,2H),2.92(t,J＝6.4Hz,2H),2.03-1.88(m,4H)；13C NMR(CDCl3)δ:145.3,140.3,134.2,128.5,126.5,124.7,113.8,44.8,24.5,23.0,21.0.
实施例47
9,10-二氢蒽和1,2,3,4-四氢蒽的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000223
将史莱克管中的气体环境置换为氮气环境，加入蒽0.25mmol，醋酸钯0.025mmol，乙酸乙酯2mL，水0.55mmol，搅拌下加入频哪醇硼烷0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以68％收率得到9,10-二氢蒽为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.32-7.26(m,4H),7.22-7.16(m,4H),3.94(s,4H)；13C NMR(CDCl3)δ:136.7,127.4,126.1,36.1；以11％收率得到1,2,3,4-四氢蒽为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.73-7.67(m,2H),7.53(s,1H),7.38-7.31(m,2H),3.00-2.93(m,4H),1.90-1.81(m,4H)；13C NMR(CDCl3)δ:136.2,132.1,126.9,126.6,124.9,29.8,13.4.
实施例48
1-苯基乙醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000231
将史莱克管中的气体环境置换为氮气环境，加入苯乙酮0.25mmol，醋酸钯0.0075mmol，二氯甲烷0.5mL，水0.275mmol，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以86％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.39-7.31(m,4H),7.29-7.24(m,1H),4.88(q,J＝6.4Hz,1H),1.96(br,s,1H),1.49(d,J＝6.5Hz,3H)；13C NMR(CDCl3)δ:145.8,128.5,127.4,125.3,70.4,25.1.
实施例49
苯甲醇的制备，氢化反应的反应式如下式所示：
Figure BDA0002317747700000232
将史莱克管中的气体环境置换为氮气环境，加入苯甲醛0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以93％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.40-7.32(m,4H),7.40-7.26(m,1H),4.68(s,2H),2.08(br,s,1H)；13C NMR(CDCl3)δ:140.8,128.5,127.6,127.0,65.3.
实施例50
N-二苯甲基苯胺的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000233
将史莱克管中的气体环境置换为氮气环境，加入N-二苯亚甲基苯胺0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，甲醇0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以93％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.37-7.26(m,8H),7.23(tt,J＝7.1,1.6Hz,2H),7.12-7.06(m,2H),6.67(t,J＝7.3Hz,1H),6.52(dd,J＝8.6,1.0Hz,2H),5.48(s,1H),4.20(br,s,1H)；13C NMR(CDCl3)δ:147.3,142.9,129.1,128.7,127.4,127.3,117.6,113.4,63.0.
实施例51
二苯基甲胺的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000241
将史莱克管中的气体环境置换为氮气环境，加入二苯甲酮亚胺0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以67％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.36(d,J＝7.4Hz,4H),7.30(t,J＝7.3Hz,4H),7.21(t,J＝7.3Hz,2H),5.20(s,1H),1.81(s,2H)；13C NMR(CDCl3)δ:145.6,128.4,126.9,126.859.7.
实施例52
1,2-二苯肼的制备，经氢化反应制得的产物的结构式如下式所示：
PhHN-NHPh
将史莱克管中的气体环境置换为氮气环境，加入偶氮苯0.25mmol，醋酸钯0.00025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.25mmol，水0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以67％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.20(t,J＝8.0Hz,4H),6.86-6.80(m,6H),5.57(br,s,2H)；13C NMR(CDCl3)δ:148.8,129.3,119.9,112.3.
实施例53
苯胺的制备，经氢化反应制得的产物的结构式如下式所示：
PhNH2
将史莱克管中的气体环境置换为氮气环境，加入硝基苯0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.825mmol，水0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，率得到目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.15(t,J＝7.8Hz,2H),6.76(t,J＝7.4Hz,1H),6.68(d,J＝7.6Hz,2H),3.65(br,s,2H)；13C NMR(CDCl3)δ:146.3,129.3,118.5,115.1.
实施例54
3-苯基丙醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000251
将史莱克管中的气体环境置换为氮气环境，加入环氧苯乙烯0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，水0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以86％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.34-7.27(m,2H),7.25-7.19(m,3H),3.84(t,J＝6.6Hz,2H),2.86(t,J＝6.6Hz,2H),1.59(br,s,1H)；13C NMR(CDCl3)δ:138.5,129.0,128.5,126.4,63.6,39.1.
实施例55
苄胺盐酸盐的制备，氢化反应的反应式如下式所示：
Figure BDA0002317747700000252
将史莱克管中的气体环境置换为氮气环境，加入苯甲腈0.25mmol，醋酸钯0.025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.825mmol，浓盐酸50微升，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以98％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CD3OD)δ:7.53-7.36(m,5H),4.92(br,s,3H),4.13(s,2H)；13C NMR(CD3OD)δ:133.1,128.8,128.8,128.7,43.0.
实施例56
肉桂酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000253
将史莱克管中的气体环境置换为氮气环境，加入苯丙炔酸0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.25mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以81％收率得到的目标产物为白色固体(产物为顺式和反式的混合物，顺式与反式的比例为6：1)。该化合物的核磁表征如下：1H NMR(CDCl3)δ:(Z)11.03,(br,s,1H),7.63-7.57(m,2H),7.38-7.29(m,3H),7.06(d,J＝12.6Hz,1H),5.96(d,J＝12.7Hz,1H)；(E)11.03,(br,s,1H),7.78(d,J＝16.0Hz,1H),7.56-7.50(m,2H),7.43-7.38(m,3H),6.44(d,J＝16.0Hz,1H)；13C NMR(CDCl3)δ:(Z)171.6,145.8,134.3,129.9,129.4,128.1,118.7；(E)174.4,147.2,134.3,130.8,128.9,128.4,117.2.
实施例57
氢化肉桂酸的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000261
将史莱克管中的气体环境置换为氮气环境，加入苯丙炔酸0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.525mmol，水0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以71％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:11.34(br,s,1H),7.33-7.26(m,2H),7.25-7.17(m,3H),2.96(t,J＝7.9Hz,2H),2,69(t,J＝8.0Hz,2H)；13C NMR(CDCl3)δ:179.4,140.1,128.5,128.2,126.4,35.6,30.5.
实施例58
(Z)-肉桂醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000262
将史莱克管中的气体环境置换为氮气环境，加入3-苯基-2-丙炔-1-醇0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.25mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以78％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.34(t,J＝7.6Hz,2H),7.25(t,J＝7.3Hz,1H),7.20(d,J＝7.2Hz,2H),6.56(d,J＝11.7Hz,1H),5.86(dt,J＝11.8,6.4Hz,1H),4.43(dd,J＝6.4,1.6Hz,2H),4.31(dd,J＝5.7,1.3Hz,0.1H,E),1.77(br,s,1H)；13C NMR(CDCl3)δ:136.5,131.1,130.9,128.7,128.2,127.2,59.6.
实施例59
氢化肉桂醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000263
将史莱克管中的气体环境置换为氮气环境，加入3-苯基-2-丙炔-1-醇0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.525mmol，甲醇0.275mmol室温条件下反应12h，反应完成后得到的反应液经过柱层析，以88％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.31-7.25(m,2H),7.24-7.16(m,3H),3.67(t,J＝6.4Hz,2H),2.71(t,J＝7.5Hz,2H),1.94-1.85(m,2H),1.53(br,s,1H)；13C NMR(CDCl3)δ:141.8,128.4,128.4,125.8,62.2,34.2,32.0.
实施例60
(Z)-1,2-二苯基乙烯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000271
将史莱克管中的气体环境置换为氮气环境，加入1,2-二苯基乙炔0.25mmol，醋酸钯0.0005mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.25mmol，水0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以90％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.28-7.15(m,10H),6.59(s,2H)；13C NMR(CDCl3)δ:137.2,130.2,128.8,128.2,127.1.
实施例61
1,2-二苯基乙烷的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000272
将史莱克管中的气体环境置换为氮气环境，加入1,2-二苯基乙炔0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.525mmol，水0.825mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以71％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.31-7.24(m,4H),7.21-7.14(m,6H),2.91(s,4H)；13C NMR(CDCl3)δ:141.8,128.4,128.3,125.9,37.9.
实施例62
4-乙烯基联苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000273
将史莱克管中的气体环境置换为氮气环境，加入4-乙炔基联苯0.25mmol，醋酸钯0.002mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.25mmol，水0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以63％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.61-7.54(m,4H),7.47(d,J＝8.3Hz,2H),7.43(t,J＝7.8Hz,2H),7.33(tt,J＝7.4,1.2Hz,1H),6.75(dd,J＝17.6,10.9Hz,1H),5.78(dd,J＝17.6,0.7Hz,1H),5.26(dd,J＝10.9,0.6Hz,1H)；13C NMR(CDCl3)δ:140.7,140.6,136.6,136.4,128.8,127.3,127.2,127.0,126.9,126.6,113.9.
实施例63
4-乙基联苯的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000281
将史莱克管中的气体环境置换为氮气环境，加入4-乙炔基联苯0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.525mmol，水0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以77％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.60-7.55(m,2H),7.51(d,J＝8.2Hz,2H),7.41(t,J＝7.4Hz,2H),7.31(tt,J＝7.4,1.2Hz,1H),7.27(d,J＝8.2Hz,2H),2.69(q,J＝7.6Hz,2H),1.27(t,J＝7.6Hz)；13C NMR(CDCl3)δ:143.4,141.2,138.6,128.7,128.3,127.1,127.0,126.9,28.5,15.6.
实施例64
4-硝基苯甲醇的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000282
将史莱克管中的气体环境置换为氮气环境，加入4-硝基苯甲醛0.25mmol，醋酸钯0.00125mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.35mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以81％收率得到的目标产物为黄色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:8.23(d,J＝8.3Hz,2H),7.54(d,J＝8.2Hz,2H),4.84(s,2H),1.90(br,s,1H)；13C NMR(CDCl3)δ:148.1,147.3,127.0,123.7,64.0.
实施例65
1-(2-硝基苯)-2-苯肼的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000283
将史莱克管中的气体环境置换为氮气环境，加入1-(2-硝基苯)-2-苯基二氮烯0.25mmol，醋酸钯0.0025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.275mmol，甲醇0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以97％收率得到的目标产物为橙色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:9.10(br,s,1H),8.17(d,J＝8.4Hz,1H),7.46-7.37(m,2H),7.23(t,J＝7.8Hz,2H),6.90(t,J＝7.4Hz,1H),6.81(d,J＝7.9Hz,2H),6.79-6.74(m,1H),5.80(br,s,1H)；13C NMR(CDCl3)δ:146.2,146.6,136.4,131.8,129.4,126.3,120.9,117.6,114.6,112.5,.
实施例66
2-乙酰基苯胺的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000291
将史莱克管中的气体环境置换为氮气环境，加入2-硝基苯乙酮0.25mmol，醋酸钯0.005mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.775mmol，水0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以87％收率得到的目标产物为淡黄色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.70(dd,J＝8.3,1.5Hz,1H),7.26(td,J＝7.7,1.5Hz,1H),6.66-6.61(m,2H),6.27(br,s,2H),2.57(s,3H)；13C NMR(CDCl3)δ:200.7,150.2,134.3,132.0,118.2,117.1,115.7,27.8.
实施例67
6-氨基喹啉的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000292
将史莱克管中的气体环境置换为氮气环境，加入6-硝基喹啉0.25mmol，醋酸钯0.005mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.775mmol，水0.55mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以>99％收率得到的目标产物为淡黄色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:8.64(dd,J＝4.2,1.52Hz,1H),7.90(d,J＝9.0Hz,1H),7.86(d,J＝8.2Hz,1H),7.24(dd,J＝8.3,4.2Hz,1H),7.13(dd,J＝8.9,2.6Hz,1H),6.86(d,J＝2.5Hz,1H),4.00(br,s,2H)；13C NMR(CDCl3)δ:146.7,144.6,143.3,133.7,130.4,129.7,121.5,121.3,107.3.
实施例68
3-乙酰基-1,2-二氢喹啉的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000293
将史莱克管中的气体环境置换为氮气环境，加入3-乙酰基喹啉0.25mmol，醋酸钯0.025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.55mmol，甲醇2.75mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以57％收率得到的目标产物为白色固体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.29(d,J＝6.0Hz,1H),7.10-7.03(m,2H),6.93(td,J＝7.4,1.1Hz,1H),6.64(d,J＝7.9Hz,1H),6.51(br,s,1H),3.76(s,2H),2.25(s,3H)；13C NMR(CDCl3)δ:195.0,138.8,136.0,130.0,127.0,123.6,121.9,114.9,110.1,25.0,24.1.
实施例69
4-(1-羟基乙基)苯甲腈的制备，经氢化反应制得的产物的结构式如下式所示：
Figure BDA0002317747700000301
将史莱克管中的气体环境置换为氮气环境，加入4-乙酰基苯甲腈0.25mmol，醋酸钯0.025mmol，二氯甲烷0.5mL，搅拌下加入频哪醇硼烷0.55mmol，醋酸0.275mmol，室温条件下反应12h，反应完成后得到的反应液经过柱层析，以89％收率得到的目标产物为无色液体。该化合物的核磁表征如下：1H NMR(CDCl3)δ:7.62(d,J＝8.4Hz,2H),7.48(d,J＝8.2Hz,2H),4.95(q,J＝6.5Hz,1H),2.41(br,s,1H),1.49(d,J＝6.5Hz,3H)；13C NMR(CDCl3)δ:151.1,132.2,126.0,118.8,110.8,69.5,25.3.
以上所述，仅为本发明的较佳实施例，并不用以限制本发明，本发明的专利保护范围以权利要求书为准，凡是运用本发明的说明书内容所作的等同结构变化，同理均应包含在本发明的保护范围内。

Claims (8)

1.一种氢化反应方法，其特征在于，包括以下步骤：
氢受体化合物、频哪醇硼烷、催化剂在质子氢存在的条件下于溶剂中进行氢转移反应，使得氢受体化合物进行氢化反应；
所述催化剂为醋酸钯；
所述氢受体化合物包含碳碳双键、碳碳三键、碳氧双键、碳氮双键、氮氮双键、碳氮三键、环氧中的一种或两种以上的官能团；
所述氢受体化合物自身含质子氢，所述质子氢由氢受体化合物自身提供，和/或通过质子性溶剂提供；
或者，所述氢受体化合物自身不含质子氢，所述质子氢通过质子性溶剂提供。
2.根据权利要求1所述的氢化反应方法，其特征在于，所述质子氢由羧酸、醇、酚、胺、酰胺、水、氢气中的一种或两种以上提供。
3.根据权利要求1所述的氢化反应方法，其特征在于，所述氢受体化合物选自式Ⅰ～式V、式VII～式Ⅸ所示的化合物、环烯烃、杂环烯烃、稠环烯烃，或为式Ⅰ～式V、式VII～式Ⅸ、环烯烃、杂环烯烃、稠环烯烃中的两种或两种以上拼接形成的拼接化合物；
Figure FDA0003953966910000011
式中，
R1～R4各自独立地选自氢、芳基、R21取代芳基、烷基、R21取代烷基、环烷基、杂环烷基、R21取代环烷基；
R5、R6、R10、R17～R20各自独立地选自氢、芳基、R21取代芳基、烷基、R21取代烷基、环烷基、杂环烷基、R21取代环烷基；
R7～R9、R11～R12、R14～R16各自独立地选自芳基、R21取代芳基、烷基、R21取代烷基、环烷基、杂环烷基、R21取代环烷基；
其中，所述R21选自苯、R22取代苯、C1～C4烷基、R22取代C1～C4烷基、C1～C4烷氧基、R22取代C1～C4烷氧基、卤素、氰、硝基、氨基、亚氨基、羟基、羧基中的一种或两种以上，所述R22选自卤素、氰、硝基、氨基、羟基、羧基中的一种或两种以上；
且R1～R22中的两个或多个取代基可以相连形成环。
4.根据权利要求1所述的氢化反应方法，其特征在于，所述氢受体化合物的结构式如下所示：
Figure FDA0003953966910000021
5.根据权利要求1～4任一项所述的氢化反应方法，其特征在于，所述氢转移反应的反应温度为5～40℃。
6.根据权利要求1～4任一项所述的氢化反应方法，其特征在于，所述氢受体化合物与频哪醇硼烷的摩尔比为1:(1～3.3)；
所述氢受体化合物与质子供体的摩尔比为1：(1～110)。
7.根据权利要求1～4任一项所述的氢化反应方法，其特征在于，所述氢受体化合物与催化剂的摩尔比为100:(0.1～10)。
8.根据权利要求1～4任一项所述的氢化反应方法，其特征在于，所述溶剂为二氯甲烷、乙酸乙酯、三氯甲烷、甲醇、乙醇、1，2-二氯乙烷、甲苯、四氢呋喃、乙醚、乙腈、1，4-二氧六环、叔丁基甲基醚、丙酮、水中的一种或两种以上的混合。
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