CN114702437B - 一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法 - Google Patents

一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法 Download PDF

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CN114702437B
CN114702437B CN202210398692.4A CN202210398692A CN114702437B CN 114702437 B CN114702437 B CN 114702437B CN 202210398692 A CN202210398692 A CN 202210398692A CN 114702437 B CN114702437 B CN 114702437B
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triphenylphosphine
trifluoromethanesulfonate
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沈志良
褚雪强
陈玉兰
张斯旋
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Nanjing Tech University
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Abstract

本发明公开了一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，将鏻盐化合物和末端炔烃化合物在钯催化剂、铜催化剂和碱的作用下，于溶剂中反应，得到目标产物。本发明制备方法反应条件温和，具有后处理简单、步骤绿色、污染低、经济效益高等特点。

Description

一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法
技术领域
本发明属于有机化合物合成技术领域，具体涉及到一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法。
背景技术
作为实现C(sp2)-C(sp)键构建的有效手段，钯催化的炔烃的Sonogashira反应在有机合成中起着举足轻重的作用。生成的芳基/乙烯基取代的内炔是一种用途广泛的构筑单元，在材料科学、药物化学、农业化学和天然产物合成等领域有着广泛的应用。一般来说，Sonogashira反应通常采用芳基卤化物或类卤化物作为亲电偶联试剂。近几十年来，二芳基碘盐、芳基重氮盐、四芳基卤化膦、芳基/苄基铵盐和芳基锍盐也被证明是钯催化偶联反应的有效的和潜在的亲电偶联试剂。
近年来，含氮杂环鏻盐受到了广泛的关注，因为它们被发现是杂芳化反应的多功能亲电试剂，能够通过各种有机反应引入杂环骨架，从而为含氮杂环化合物的合成提供了一个新的途径。然而，虽然杂环鏻盐与芳基硼酸和烷基锌试剂发生了Suzuki偶联反应和Negishi偶联反应，但杂环鏻盐与末端炔烃的Sonogashira偶联反应至今未见报道。此外，由吡啶、二嗪和其他杂环衍生的杂环鏻盐具有较好的热稳定性和较长的保存期，它是通过杂环化合物与三芳基磷的C-H键官能化反应合成得到，特别是在吡啶环的C4-位进行三芳基磷化，这是用常规方法难以实现的。
发明内容
本部分的目的在于概述本发明的实施例的一些方面以及简要介绍一些较佳实施例。在本部分以及本申请的说明书摘要和发明名称中可能会做些简化或省略以避免使本部分、说明书摘要和发明名称的目的模糊，而这种简化或省略不能用于限制本发明的范围。
鉴于上述和/或现有技术中存在的问题，提出了本发明。
本发明的其中一个目的是提供一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，反应条件温和，具有后处理简单、步骤绿色、污染低、经济效益高等特点。
为解决上述技术问题，本发明提供了如下技术方案：一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，包括，将式Ⅰ所示的鏻盐化合物和式Ⅱ所示的末端炔烃化合物在钯催化剂、铜催化剂和碱的作用下，于溶剂中反应，得到式Ⅲ所示的化合物；
Figure BDA0003598682190000021
Figure BDA0003598682190000022
Figure BDA0003598682190000023
其中，式Ⅰ、式Ⅲ中的Ar包括吡啶、卤素取代吡啶、甲基取代吡啶、甲氧基取代吡啶、氰基取代吡啶、酯基取代吡啶、连吡啶、喹啉、吡嗪、甲基取代吡嗪、氯雷他定、喹喔啉中的一种；
式Ⅱ、式Ⅲ中的R包括卤素取代苯基、甲基取代苯基、甲氧基取代苯基、叔丁基取代苯基、三氟甲基取代苯基、酯基取代苯基、氨基取代苯基、联苯、噻吩、萘、戊烷中的一种。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述鏻盐化合物选自4-三苯基鏻吡啶)三氟甲磺酸盐、(3-甲氧羰基-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-甲氧羰基-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-氰基-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-甲氧基-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-甲基-4-三苯基鏻基吡啶)三氟甲磺酸盐、(3-苯基-4-三苯基鏻吡啶)三氟甲磺酸盐、(5,6,7,8-四氢喹啉-4-三苯基鏻)三氟甲磺酸盐、(3-氟-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-氯-4-三苯基鏻吡啶)三氟甲磺酸盐、2-(对甲苯基)-4-三苯基鏻吡啶)三氟甲磺酸盐、(2-(2-吡啶)-4-三苯基鏻吡啶)三氟甲磺酸盐、(4-三苯基鏻喹啉)三氟甲磺酸盐、(2-三苯基鏻吡嗪)三氟甲磺酸盐、(5,6-二甲基-2-三苯基鏻吡嗪)三氟甲磺酸盐、(2-三苯基鏻喹喔啉)三氟甲磺酸盐、(4-三苯基鏻氯雷他定)三氟甲磺酸盐中的一种。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述末端炔烃化合物选自溴苯、4-乙炔基苯甲酸甲酯、1-乙炔基-4-(三氟甲基)苯、1-乙炔基-4-氟苯、1-氯-4-乙炔苯、1-乙炔基-2-甲基苯、1-乙炔基-3-甲基苯、1-乙炔基-4-甲基苯、1-(叔丁基)-4-乙炔基苯、1-乙炔基-4-甲氧基苯、4-乙炔基-N,N-二甲基苯胺、6-乙炔基-4,4-二甲基二氢苯并噻喃、4-乙炔基-1,1'-联苯、3-乙炔基噻吩、庚-1-炔中的一种。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述鏻盐化合物和所述末端炔烃化合物的摩尔比为1：1.5～3。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述钯催化剂包括双三苯基膦二氯化钯、溴化钯、四三苯基膦钯、乙酰丙酮钯、三(二亚苄基丙酮)二钯、烯丙基氯化钯、[1,3-双(2,6-二异丙基苯基)咪唑-2-亚基](3-氯吡啶)二氯化钯中的一种；所述钯催化剂的添加量为0～0.1当量。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述铜催化剂包括碘化亚铜、氯化亚铜、溴化亚铜、氰化亚铜、氯化铜、醋酸铜中的一种；所述铜催化剂的添加量为0～0.1当量。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述碱为有机碱或无机碱；所述碱的添加量为1.5当量；
所述有机碱选自三乙胺、咪唑、三乙烯二胺、四甲基乙二胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯、N,N-二异丙基乙胺中的一种；
所述无机碱选自碳酸铯、碳酸钾、氢氧化钠、醋酸钠的一种。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述溶剂包括1，4-二氧六环、N-甲基吡咯烷酮、乙腈、乙醇、1,2-二氯乙烷、四氢吡喃、甲苯、丙酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、N,N-二甲基丙烯基脲、1-丁基-3-甲基咪唑四氟硼酸盐、水中的一种。
作为本发明杂芳基鏻盐与末端炔烃的Sonogashira偶联方法的一种优选方案，其中：所述于溶剂中反应，反应温度为0～100℃，反应时间为6～24h。
综上，本发明的化学方程式如下所示：
Figure BDA0003598682190000031
与现有技术相比，本发明具有如下有益效果：
本发明提供了一种从简单易得鏻盐与末端炔烃原料出发合成炔基吡啶或二嗪类化合物的新方法，拓展了此类化合物的制备底物范围；该反应使用了便宜易得的末端炔烃化合物作为偶联底物，使得反应具有了操作便捷性和步骤经济性；本发明制备方法反应条件温和，具有后处理简单、步骤绿色、污染低、经济效益高等特点。
附图说明
为了更清楚地说明本发明实施例的技术方案，下面将对实施例描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动性的前提下，还可以根据这些附图获得其它的附图。其中：
图1为本发明实施例1的目标产物4-(苯乙炔基)吡啶的氢谱；
图2为本发明实施例1的目标产物4-(苯乙炔基)吡啶的碳谱。
图3为本发明实施例2的目标产物2-(苯乙炔基)吡嗪的氢谱；
图4为本发明实施例2的目标产物2-(苯乙炔基)吡嗪的碳谱。
图5为本发明实施例3的目标产物N,N-二甲基-4-(吡啶-4-乙炔基)苯胺的氢谱；
图6为本发明实施例3的目标产物N,N-二甲基-4-(吡啶-4-乙炔基)苯胺的碳谱。
具体实施方式
为使本发明的上述目的、特征和优点能够更加明显易懂，下面结合说明书实施例对本发明的具体实施方式做详细的说明。
在下面的描述中阐述了很多具体细节以便于充分理解本发明，但是本发明还可以采用其他不同于在此描述的其它方式来实施，本领域技术人员可以在不违背本发明内涵的情况下做类似推广，因此本发明不受下面公开的具体实施例的限制。
其次，此处所称的“一个实施例”或“实施例”是指可包含于本发明至少一个实现方式中的特定特征、结构或特性。在本说明书中不同地方出现的“在一个实施例中”并非均指同一个实施例，也不是单独的或选择性的与其他实施例互相排斥的实施例。
如无特别说明，实施例中所采用的原料均为商业购买。
实施例1
(1)将配有磁力搅拌子的20mL Schlenk管放在烘箱中干燥一小时，拿出后趁热塞上橡胶塞并插上一个氮气球。冷却后，向其中依次添加(4-三苯基鏻吡啶)三氟甲磺酸盐(244.7mg，0.5mmol，1equiv.)、Pd(PPh3)2Cl2(35.1mg，0.05mmol，0.1equiv.)、CuI(9.5mg，0.05mmol，0.1equiv.)，接着将封管抽换氮气三次，随后向Schlenk管中依次加入超干N-甲基吡咯烷酮溶剂(2mL)，DIPEA(96.9mg，0.75mmol，1.5equiv.)和苯乙炔(101.1mg，1mmol，1.5equiv.)；混合物在100℃下搅拌12小时；
(2)随后使用饱和氯化铵溶液进行淬灭、使用乙酸乙酯进行萃取；萃取液经饱和食盐水洗涤、无水硫酸钠干燥后，通过旋蒸除去萃取液，粗产物通过硅胶柱层析法提纯，柱层析分离条件：固定相为300～400目硅胶粉，流动相为乙酸乙酯(A)和石油醚(B)，流动相变化程序(A:B)为1：5，最终得到71.1mg的目标产物4-(苯乙炔基)吡啶，该化合物结构式为：
Figure BDA0003598682190000051
对上述4-(苯乙炔基)吡啶进行表征，如图1和2所示，结果为：黄色固体；1H NMR(400MHz,CDCl3):δ8.64-8.57(m,2H),7.58-7.53(m,2H),7.41-7.36(m,5H)ppm.13C NMR(100MHz,CDCl3):δ149.7,131.9,131.5,129.2,128.5,125.5,122.1,94.0,86.6ppm.HRMS(ESI,m/z):[M+H]+,calcd.for C13H10N+:180.0808,found:180.0807.FTIR(KBr,neat):ν3026,2222,1600,1588,1576,1537,828,692cm-1.
根据表征数据可知，制得的反应产物为4-(苯乙炔基)吡啶(纯度＞98％)；对产品产率进行计算，结果为67％。
实施例2
(1)将配有磁力搅拌子的20mL Schlenk管放在烘箱中干燥一小时，拿出后趁热塞上橡胶塞并插上一个氮气球。冷却后，向其中依次添加(2-三苯基鏻吡嗪)三氟甲磺酸盐(245.2mg，0.5mmol，1equiv.)、Pd(PPh3)2Cl2(35.1mg，0.05mmol，0.1equiv.)、CuI(9.5mg，0.05mmol，0.1equiv.)，接着将封管抽换氮气三次，随后向Schlenk管中依次加入超干N-甲基吡咯烷酮溶剂(2mL)，DIPEA(96.9mg，0.75mmol，1.5equiv.)和苯乙炔(101.1mg，1mmol，2equiv.)；混合物在100℃下搅拌12小时；
(2)随后使用饱和氯化铵溶液进行淬灭、使用乙酸乙酯进行萃取；萃取液经饱和食盐水洗涤、无水硫酸钠干燥后，通过旋蒸除去萃取液，粗产物通过硅胶柱层析法提纯，柱层析分离条件：固定相为300～400目硅胶粉，流动相为乙酸乙酯(A)和石油醚(B)，流动相变化程序(A:B)为1：5，最终得到44.8mg的目标产物2-(苯乙炔基)吡嗪，该化合物结构式为：
Figure BDA0003598682190000061
对上述2-(苯乙炔基)吡嗪进行表征，如图3和4所示，结果为：棕色固体；1H NMR(400MHz,CDCl3):δ8.75(d,J＝1.5Hz,1H),8.62-8.55(m,1H),8.47(d,J＝2.5Hz,1H),7.67-7.58(m,2H),7.46-7.32(m,3H)ppm.13C NMR(100MHz,CDCl3):δ147.7,144.4,142.7,140.3,132.1,129.5,128.5,121.4,93.2,85.7ppm.HRMS(ESI,m/z):[M+H]+,calcd.for C12H9N2 +:181.0760,found:181.0764.FTIR(KBr,neat):ν3062,2221,1599,1561,1515,1492,757,691cm-1.
根据表征数据可知，制得的反应产物为2-(苯乙炔基)吡嗪(纯度＞98％)；对产品产率进行计算，结果为50％。
实施例3
(1)将配有磁力搅拌子的20mL Schlenk管放在烘箱中干燥一小时，拿出后趁热塞上橡胶塞并插上一个氮气球。冷却后，向其中依次添加(4-三苯基鏻吡啶)三氟甲磺酸盐(244.7mg，0.5mmol，1equiv.)、Pd(PPh3)2Cl2(35.1mg，0.05mmol，0.1equiv.)、CuI(9.5mg，0.05mmol，0.1equiv.)，接着将封管抽换氮气三次，随后向Schlenk管中依次加入超干N-甲基吡咯烷酮溶剂(2mL)，DIPEA(96.9mg，0.75mmol，1.5equiv.)和4-乙炔基-N,N-二甲基苯胺(145.2mg，1mmol，2equiv.)；混合物在100℃下搅拌12小时；
(2)随后使用饱和氯化铵溶液进行淬灭、使用乙酸乙酯进行萃取；萃取液经饱和食盐水洗涤、无水硫酸钠干燥后，通过旋蒸除去萃取液，粗产物通过硅胶柱层析法提纯，柱层析分离条件：固定相为300～400目硅胶粉，流动相为乙酸乙酯(A)和石油醚(B)，流动相变化程序(A:B)为1：5，最终得到45.3mg的目标产物N,N-二甲基-4-(吡啶-4-乙炔基)苯胺，该化合物结构式为：
Figure BDA0003598682190000071
对上述N,N-二甲基-4-(吡啶-4-乙炔基)苯胺进行表征，如图5和6所示，结果为：黄色固体；1H NMR(400MHz,CDCl3):δ8.54(dd,J＝4.5,1.5Hz,2H),7.42(d,J＝9.0Hz,2H),7.37-7.30(m,2H),6.66(d,J＝7.0Hz,2H),3.01(s,6H)ppm.13C NMR(100MHz,CDCl3):δ150.6,149.5,133.2,132.4,125.2,111.7,108.4,96.0,85.2,40.1ppm.HRMS(ESI,m/z):[M+H]+,calcd.for C15H15N2 +:223.1230,found:223.1230.FTIR(KBr,neat):ν 3040,2899,2209,1610,1588,819,725,698cm-1.
根据表征数据可知，制得的反应产物为N,N-二甲基-4-(吡啶-4-乙炔基)苯胺(纯度＞98％)；对产品产率进行计算，结果为41％。
实施例4
实施例4与实施例1基本相同，差别之处在于步骤(1)中使用三乙胺替换DIPEA作碱且溶剂不同，具体如下表1所示：
表1
Figure BDA0003598682190000072
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Figure BDA0003598682190000081
从表1中可以看出，相同反应条件下，使用不同溶剂，如：1，4-二氧六环、乙腈、乙醇、1,2-二氯乙烷、四氢吡喃、甲苯、丙酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、N,N-二甲基丙烯基脲、1-丁基-3-甲基咪唑四氟硼酸盐、水合成4-(苯乙炔基)吡啶，产率较低；当以N-甲基吡咯烷酮作溶剂时，反应产率为19％。
实施例5
实施例5与实施例1基本相同，差别之处在于步骤(1)中使用三乙胺替换DIPEA作碱且钯催化剂不同，具体如下表2所示：
表2
Figure BDA0003598682190000082
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Figure BDA0003598682190000091
从表2中可以看出，相同反应条件下，使用不同钯催化剂，如：溴化钯、四三苯基膦钯、乙酰丙酮钯、三(二亚苄基丙酮)二钯、烯丙基氯化钯二聚体、[1,3-双(2,6-二异丙基苯基)咪唑-2-亚基](3-氯吡啶)二氯化钯合成4-(苯乙炔基)吡啶，产率较低；当以双三苯基膦二氯化钯作催化剂时，反应产率为19％。
实施例6
实施例6与实施例1基本相同，差别之处在于步骤(1)中碱不同，具体如下表3所示：
表3
碱 产率(％)
Et3N 19
TMEDA 44
DBU 24
DABCO 37
imidazole <5
DMAP 31
Cs2CO3 <5
K2CO3 17
NaOH 21
NaOAc 44
DIPEA 67
从表3中可以看出，相同反应条件下，使用不同碱，如：三乙胺、咪唑、三乙烯二胺、四甲基乙二胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯、碳酸铯、碳酸钾、氢氧化钠、醋酸钠合成4-(苯乙炔基)吡啶，产率较低；当以N,N-二异丙基乙胺作碱时，反应产率为67％。
实施例7
实施例7与实施例1基本相同，差别之处在于步骤(1)中铜催化剂不同，具体如下表4所示：
表4
铜催化剂 产率(％)
CuI 67
CuBr 47
CuCl 19
CuCN 18
CuCl2 20
Cu(OAc)2 6
从表4中可以看出，相同反应条件下，对不同的共催化剂，如：碘化亚铜、氯化亚铜、溴化亚铜、氰化亚铜、氯化铜、醋酸铜中合成4-(苯乙炔基)吡啶，以碘化亚铜效果最优，产率最高为67％。
实施例8
实施例8与实施例1基本相同，差别之处在于步骤(2)中，中苯乙炔、二三苯基膦二氯化钯和碘化亚铜的当量不同，具体如下表5所示：
表5
Figure BDA0003598682190000101
Figure BDA0003598682190000111
从表5中可以看出，相同反应条件下，对不同的苯乙炔、二三苯基膦二氯化钯和碘化亚铜的当量，如：苯乙炔(1.5equiv、2equiv、3equiv)、二三苯基膦二氯化钯(0.1equiv、0.05equiv、0equiv)、碘化亚铜(0.1equiv、0.05equiv、0equiv)，以苯乙炔(2equiv)、二三苯基膦二氯化钯(0.1equiv)、碘化亚铜(0.1equiv)效果最优，产率最高为79％。
实施例9
实施例9与实施例1基本相同，差别之处在于步骤(1)中，芳基鏻盐和末端炔烃不同，具体如下表6所示：
表6
Figure BDA0003598682190000112
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Figure BDA0003598682190000121
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Figure BDA0003598682190000131
本发明提供了一种钯催化的杂环鏻盐与末端炔烃的Sonogashira偶联反应，该反应在PdCl2(PPh3)2和CuI的催化下进行，以中等至良好的产率得到相应的炔基取代的吡啶、喹啉、吡嗪和喹恶啉等产物；本发明制备方法反应条件温和，具有后处理简单、步骤绿色、污染低、经济效益高等特点。
应说明的是，以上实施例仅用以说明本发明的技术方案而非限制，尽管参照较佳实施例对本发明进行了详细说明，本领域的普通技术人员应当理解，可以对本发明的技术方案进行修改或者等同替换，而不脱离本发明技术方案的精神和范围，其均应涵盖在本发明的权利要求范围当中。

Claims (5)

1.一种杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，其特征在于：包括，
将式Ⅰ所示的鏻盐化合物和式Ⅱ所示的末端炔烃化合物在钯催化剂、铜催化剂和碱的作用下，于溶剂中反应，得到式Ⅲ所示的化合物；
Figure QLYQS_1
（式Ⅰ）；
Figure QLYQS_2
（式Ⅱ）；
Figure QLYQS_3
（式Ⅲ）；
其中，式Ⅰ、式Ⅲ中的Ar选自吡啶、卤素取代吡啶、甲基取代吡啶、甲氧基取代吡啶、氰基取代吡啶、酯基取代吡啶、连吡啶、喹啉、吡嗪、甲基取代吡嗪、氯雷他定、喹喔啉中的一种；
式Ⅱ、式Ⅲ中的R选自卤素取代苯基、甲基取代苯基、甲氧基取代苯基、叔丁基取代苯基、三氟甲基取代苯基、酯基取代苯基、氨基取代苯基、联苯、噻吩、萘、戊烷中的一种；
其中，所述钯催化剂选自双三苯基膦二氯化钯、溴化钯、烯丙基氯化钯中的一种；
所述铜催化剂选自碘化亚铜、氯化亚铜、溴化亚铜、氰化亚铜、氯化铜中的一种；
所述碱为有机碱或无机碱；所述有机碱选自三乙胺、三乙烯二胺、四甲基乙二胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯、N,N-二异丙基乙胺中的一种；所述无机碱选自碳酸钾、氢氧化钠、醋酸钠的一种；
所述溶剂选自1，4-二氧六环、N-甲基吡咯烷酮、乙腈、丙酮、N,N-二甲基丙烯基脲中的一种。
2.如权利要求1所述的杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，其特征在于：所述鏻盐化合物选自4-三苯基鏻吡啶)三氟甲磺酸盐、(3-甲氧羰基-4-三苯基鏻吡啶)三氟甲磺酸盐、 (3-氰基-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-甲氧基-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-甲基-4-三苯基鏻基吡啶)三氟甲磺酸盐、 (3-氟-4-三苯基鏻吡啶)三氟甲磺酸盐、(3-氯-4-三苯基鏻吡啶)三氟甲磺酸盐、(2-(2-吡啶)-4-三苯基鏻吡啶)三氟甲磺酸盐、(4-三苯基鏻喹啉）三氟甲磺酸盐、（2-三苯基鏻吡嗪）三氟甲磺酸盐、(5,6-二甲基-2-三苯基鏻吡嗪）三氟甲磺酸盐、（2-三苯基鏻喹喔啉）三氟甲磺酸盐、(4-三苯基鏻氯雷他定)三氟甲磺酸盐中的一种。
3.如权利要求1所述的杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，其特征在于：所述末端炔烃化合物选自4-乙炔基苯甲酸甲酯、1-乙炔基-4-（三氟甲基）苯、1-乙炔基-4-氟苯、1-氯-4-乙炔苯、1-乙炔基-2-甲基苯、1-乙炔基-3-甲基苯、1-乙炔基-4-甲基苯、1-（叔丁基）-4-乙炔基苯、1-乙炔基-4-甲氧基苯、4-乙炔基-N,N-二甲基苯胺、4-乙炔基-1,1'-联苯、3-乙炔基噻吩、庚-1-炔中的一种。
4.如权利要求1~3中任一项所述的杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，其特征在于：所述鏻盐化合物和所述末端炔烃化合物的摩尔比为1：1.5~3。
5.如权利要求1~3中任一项所述的杂芳基鏻盐与末端炔烃的Sonogashira偶联方法，其特征在于：所述于溶剂中反应，反应温度为0~100 ℃，反应时间为6~24 h。
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