CN113292434B - 光催化非芳基重氮化合物和烯烃的环丙烷化反应 - Google Patents

光催化非芳基重氮化合物和烯烃的环丙烷化反应 Download PDF

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CN113292434B
CN113292434B CN202010109397.3A CN202010109397A CN113292434B CN 113292434 B CN113292434 B CN 113292434B CN 202010109397 A CN202010109397 A CN 202010109397A CN 113292434 B CN113292434 B CN 113292434B
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吕健
段得鹏
尚万送
刘永军
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Qingdao University of Science and Technology
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Abstract

本发明公开了属于有机合成技术领域的一种光催化非芳烃重氮化合物和烯烃的环丙烷化反应，制备多取代环丙烷类化合物的方法。所述方法为：以Ir光敏剂为催化剂，在蓝光LED灯的照射条件下，将非芳烃重氮化合物和烯烃完成环丙化反应，可直接生成多取代环丙烷化合物。本发明所述的光催化非芳烃重氮化合物和烯烃的环丙烷化反应，制备多取代环丙烷类化合物的方法具有科学合理，环境友好，合成方法简单，目标化合物产率高等特点。更为重要的是，该方法能单一合成环丙烷化合物，避免非芳烃重氮类化合物在过渡金属或Lewis酸等条件下，易于发生1,2‑氢转移生成不饱和羰基化合物副产物的弊端。

Description

光催化非芳基重氮化合物和烯烃的环丙烷化反应
技术领域
本发明公开了属于有机合成技术领域的一种光催化非芳烃重氮化合物和烯烃的环丙烷化反应，制备多取代环丙烷类化合物的方法。
背景技术
环丙烷类化合物是一类重要的三碳合成子，它可以发生开环反应，重排反应等，是合成一些天然产物和新型药物的重要中间体。重氮化合物在过渡金属的催化下容易形成缺电子卡宾，可以参与一系列有机合成反应(Chem.Rev.2015,115,9981-10080)。而在众多反应中，环丙烷化反应是最为重要的反应之一(Acc.Chem.Res.2016,49,115-127)。在过去二十多年里，贵金属Rh、Ru及金属Cu催化芳基重氮化合物与烯烃的环丙烷化反应已相继被报道，而β-位上带有取代基团尤其是芳基取代基的α-重氮化合物在过渡金属或Lewis酸的作用下，更易发生1,2-氢转移反应，使其无法与烯烃进行环丙烷化反应。目前，鉴于非芳香重氮化合物与烯烃的环丙烷化反应的局限性，寻找一种环境友好，操作简单，且催化合成多取代环丙烷类化合物的方法就显得的极为重要，而可见光催化恰好能够实现这一目标。
发明内容
本发明提供了一种多取代环丙烷类化合物的制备方法。
本发明提供了一种合成式(I)所示的环丙烷类化合物的制备方法，该方法包括：以铱光敏剂为催化剂，在蓝光LED灯的照射下，将式(II)所示的α-重氮酸酯化合物与式(III)所示的烯烃进行环丙烷化反应。
Figure BDA0002389433740000021
其中，R1为选自取代或未取代的C1-C10的烷基、取代或未取代的C6-C20的芳基和取代或未取代的杂环基团中的一种；R2取代基团为选自取代或未取代的C1-C10的烷基、取代或未取代的C7-C20的苄基中的一种；R3和R4为各自独立地选自氢、取代或未取代的C1-C5的烷基、取代或未取代的芳基中的一种、酯基、烷氧基和芳巯基中的一种。
优选地，相对于100摩尔份所述的α-重氮酸酯化合物，烯烃的用量为100-1000摩尔份，优选为100-500摩尔份。
优选地，相对于100摩尔份所述的α-重氮酸酯化合物，铱光敏剂用量为0.01-2摩尔份，优选为0.1-1摩尔份。
优选地，所述的Ir光敏剂为式(IV)至(IX)所示化合物中的一种。
Figure BDA0002389433740000022
优选地，所述的α-重氮酸酯化合物与烯烃的环丙烷化反应所需光源蓝光LED灯，波长范围为390-456nm，优选为456nm。
优选地，所述的α-重氮酸酯化合物与烯烃的环丙烷化反应在25-60℃的温度下搅拌进行12-36小时。
优选地，在反应后用石油醚和乙酸乙酯的混合溶剂进行柱层析。
本发明所述的合成环丙烷结构类化合物制备方法具有以下优点：
(1)可见光催化相比于过渡金属催化，具有环境友好、反应条件温和、易于操作特点；
(2)能较大程度避免非芳烃类重氮化合物1,2-氢转移生成不饱和羰基化合物；
(3)该方法适于多取代尤其是含季碳结构的环丙烷化合物；
(4)本发明所述的方法易于大规模生产。
附图说明
图1为实施例1制备的化合物3a的NMR图谱；
图2为实施例2制备的化合物3b的NMR图谱；
图3为实施例3制备的化合物3c的NMR图谱；
图4为实施例4制备的化合物3d的NMR图谱。
具体实施方式
下面采用具体的实施例对本发明进一步详细的说明：
下述实施例中所述试验方法，如无特殊说明，均为常规方法；所述试剂和材料，如无特殊说明，均可从商业途径获得。
实施例1
环丙烷类化合物3a的制备，反应方程式如下：
Figure BDA0002389433740000031
在反应瓶中分别加入化合物1a(100mmol),化合物2a(500mmol),催化剂(式(IV))(1mmol)，二氯甲烷(500mL)，N2保护条件下，蓝光LED灯照射12h。反应结束后，使用旋蒸仪去除二氯甲烷溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3a，其收率为92％(1:1d.r.)。
3a核磁数据:
1H NMR(500MHz,CDCl3):δ7.32-7.12(m,21H),4.18-4.06(m,2H),3.75-3.61(m,3H),3.19(d,J＝16.0Hz,1H),2.85(t,J＝8.5Hz,1H),2.70(d,J＝14.5Hz,1H),2.43(t,J＝8.0Hz,1H),2.04-1.98(m,2H),1.89(dd,J＝5.0,9.0Hz,1H),1.41(dd,J＝5.0,7.0Hz,1H),1.28-1.25(m,2H),1.17(t,J＝7.0Hz,3H),0.76(t,J＝7.0Hz,3H)ppm.
13C NMR(125MHz,CDCl3):δ174.6,171.5,140.4,139.4,137.0,136.7,129.3,129.2,129.1,128.7,128.4,128.3,128.1,127.9,127.0,126.6,126.4,125.9,60.9,60.3,40.4,33.6,33.4,32.7,32.0,30.9,17.9,16.7,14.1,13.7ppm.
实施例2
环丙烷类化合物3b的制备,反应方程式如下：
Figure BDA0002389433740000041
在反应瓶中分别加入化合物1a(100mmol),化合物2b(500mmol),催化剂(式(V))(1mmol)，二氯甲烷(500mL)，N2保护条件下，蓝光LED灯照射12h。反应结束后，使用旋蒸仪去除二氯甲烷溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3b，其收率为83％(8:1d.r.)。
3b核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.27–7.16(m,5H),4.06(q,J＝7.0Hz,2H),3.75(s,3H),3.34(d,J＝14.5Hz,1H),2.67(d,J＝15.0Hz,1H),1.75(d,J＝5.5Hz,1H),1.60(d,J＝5.0Hz,1H),1.36(s,3H),1.13(t,J＝7.0Hz,3H)ppm.
13C NMR(125MHz,CDCl3):δ172.7,170.8,139.2,128.6,128.3,126.3,61.1,52.3,37.9,35.0,30.6,23.0,16.1,14.2ppm.
实施例3
环丙烷类化合物3c的制备,反应方程式如下:
Figure BDA0002389433740000051
在反应瓶中加入化合物1a(100mmol),化合物2c(500mmol),催化剂(式(IV))(1mmol)，二氯甲烷(500mL)，N2保护条件下，蓝光LED灯照射12h。反应结束后，使用旋蒸仪去除二氯甲烷溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3c，其收率为74％(1.2:1d.r.)。
3c核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.32-7.12(m,11.01H),7.09(dd,J＝5.0,1.0Hz,1.05H),6.97-6.96(m,0.95H),6.89-6.82(m,2.75H),4.20-4.06(m,2.21H),3.86-3.80(m,2.05H),3.67(d,J＝14.5Hz,1.14H),3.29(d,J＝15.5Hz,0.83H),2.91–2.88(m,0.84H),2.62(d,J＝14.5Hz,0.99H),2.485(t,J＝8.0Hz,1.03H),2.21(d,J＝15.5Hz,0.84H),2.03–2.01(m,1.00H),1.96(dd,J＝9.0,4.5Hz,0.83H),1.38-1.36(m,1.88H),1.28–1.24(m,1.22H),1.18(t,J＝7.0Hz,2.46H),0.90(t,J＝7.0Hz,3.00H)ppm.
13C NMR(125MHz,CDCl3):δ170.9,140.7,140.2,139.0,129.0,128.7,128.3,128.1,127.0,126.5,126.4,126.1,126.0,124.7,124.0,61.0,60.6,39.9,34.3,33.2,31.8,27.1,26.1,20.4,18.7,14.1,13.8ppm.
实施例4
环丙烷类化合物3d的制备,反应方程式如下:
Figure BDA0002389433740000061
在反应瓶中加入化合物1a(100mmol),化合物2d(500mmol),催化剂(式(VII))(1mmol)，二氯甲烷(500mL)，N2保护条件下，蓝光LED灯照射12h。反应结束后，使用旋蒸仪去除二氯甲烷溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3d，其收率为88％(10:1d.r.)。
3d核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.25–7.14(m,5H),4.89(d,J＝47.5Hz,2H),4.09(q,J＝7.0Hz,2H),3.53(d,J＝15.0Hz,1H),2.28(d,J＝15.0Hz,1H),1.86(s,3H),1.50(d,J＝5.0Hz,1H),1.24(s,3H),1.16(t,J＝7.0Hz,3H),0.88–0.84(m,1H).
13C NMR(125MHz,CDCl3):δ173.0,146.8,140.4,128.4,128.2,126.0,113.2,60.5,35.9,35.7,35.1,22.9,20.9,19.0,14.3.
实施例5
环丙烷类化合物3e的制备,反应方程式如下:
Figure BDA0002389433740000071
在反应瓶中加入化合物1a(100mmol),化合物2e(500mmol),催化剂(式(IV))(1mmol)，二氯甲烷(500mL)，N2保护条件下，蓝光LED灯照射12h。反应结束后，使用旋蒸仪去除二氯甲烷溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3e-1和3e-2，收率分别为32％和32％。
3e-1核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.31-7.17(m,10H),4.16(q,J＝7.0Hz,2H),3.56(d,J＝15.5,1H),2.95-2.88(m,2H),1.98(dd,J＝5.5,8.0Hz,1H),1.20(t,J＝7.0Hz,3H),1.06(t,J＝6.0Hz,1H)ppm.
13C NMR(125MHz,CDCl3):δ173.3,139.8,136.8,129.0,128.9,128.2,126.7,126.0,125.6,61.1,33.2,31.9,30.0,20.3,14.1ppm.
3e-2核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.33-7.14(m,10H),4.03(m,2H),3.73(d,J＝14.5Hz,1H),2.61(d,J＝14.5Hz,1H),2.52(dd,J＝6.0,8.5Hz,1H),1.71(t,J＝6.0Hz,1H),1.36(dd,J＝5.5,8.5Hz,1H),1.04(t,J＝7.5Hz,3H)ppm.
13C NMR(125MHz,CDCl3):δ170.4,138.1,137.1,129.0,128.7,128.4,127.4,126.6,125.5,61.0,39.7,34.4,27.6,17.9,14.0ppm.
实施例6
环丙烷类化合物3f的制备，反应方程式如下：
Figure BDA0002389433740000081
在反应瓶中加入化合物1b(100mmol),化合物2a(500mmol),催化剂(式(IV))(1mmol)，二氯甲烷(500mL)，N2保护条件下，蓝光LED灯照射12h。反应结束后，使用旋蒸仪去除二氯甲烷溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3f，其收率为58％(1:1d.r.)。
3f核磁数据:
1H NMR(500MHz,CDCl3):δ7.36-7.17(m,18H),7.00-6.96(m,2H),5.20-5.14(m,2H),4.83(d,J＝12.5Hz,1H),4.62(d,J＝12.0Hz,1H),2.80(t,J＝8.0Hz,1H),2.34(t,J＝8.0Hz,1H),2.78-2.22(m,1H),1.94(t,J＝6.0Hz,1H),1.71(dd,J＝4.5,9.0Hz,1H),1.65-1.43(m,4H),1.26-1.07(m,31H),0.89-0.86(m,8H)ppm.
13C NMR(125MHz,CDCl3):δ174.8,171.9,137.2,136.9,136.3,136.0,129.3,129.0,128.5,128.3,128.1,128.0,128.0,127.8,126.7,126.5,66.4,66.1,36.0,33.3,32.6,32.2,31.9,30.7,29.7,29.6,29.6,29.4,29.3,28.5,27.8,27.5,22.7,18.1,17.5,14.1ppm.
表一：
Figure BDA0002389433740000091

Claims (5)

1.一种合成式（I）所示的环丙烷类化合物的制备方法，该方法包括：以铱光敏剂为催化剂，在蓝光LED灯的照射条件下，将式（II）所示的α-重氮酸酯化合物与式（III）所示的烯烃进行环丙烷化反应；
Figure 511345DEST_PATH_IMAGE001
其中，R1为选自C1-C10的烷基、C6-C20的芳基中的一种；R2取代基团为选自C1-C10的烷基、苄基中的一种；R3和R4为各自独立地选自氢、C1-C5的烷基、苯基、烷氧基、甲酸甲酯基和芳巯基中的一种；
相对于100摩尔份所述的α-重氮酸酯化合物，烯烃的用量为100-1000摩尔份；
铱光敏剂为式(IV)至(IX)所示化合物中的一种；
Figure DEST_PATH_IMAGE003
。
2.根据权利要求1所述的制备方法，其中，相对于100摩尔份所述的α-重氮酸酯化合物，铱光敏剂的用量为0.01-2摩尔份。
3.根据权利要求1所述的方法，其中，所述的α-重氮酸酯化合物与烯烃的环丙烷化反应所需光源为蓝光LED灯，波长范围在390-456nm。
4.根据权利要求1所述的方法，其中，所述的α-重氮酸酯化合物与烯烃的环丙烷化反应在25-60ºC的温度下搅拌进行12-36小时。
5.根据权利要求1所述的方法，其中，在反应后用石油醚和乙酸乙酯的混合溶剂进行柱层析。
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