经由Domino脱HCl/Pd(OAc)2催化的Heck反应合成查尔酮

doi:10.1016/S1872-2067(14)60247-3

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 78-85.DOI: 10.1016/S1872-2067(14)60247-3

经由Domino脱HCl/Pd(OAc)₂催化的Heck反应合成查尔酮

郭腾龙^a, 姜权彬^a, 余立坤^b, 余正坤^a

a 中国科学院大连化学物理研究所, 辽宁大连116023;
b 中国石化巴陵石化分公司技术中心化肥分析站, 湖南岳阳414003

收稿日期:2014-08-22 修回日期:2014-09-22 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 余正坤
基金资助:
国家自然科学基金(21272232).

Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction

Tenglong Guo^a, Quanbin Jiang^a, Likun Yu^b, Zhengkun Yu^a

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b Fertilizer Analysis Station of Technology Center, SINOPEC Baling Petrochemical Company, Yueyang 414003, Hunan, China

Received:2014-08-22 Revised:2014-09-22 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National Natural Science Foundation of China (21272232).

摘要/Abstract

摘要：

通过Domino脱HCl/Pd(OAc)₂催化的Heck反应实现了β-氯代烷基芳基酮、酯和酰胺与卤代芳烃的交叉偶联反应, 高效合成了查尔酮类化合物. 利用原位生成烯酮为中间体进行反应的策略, 减少副反应的发生, 从而提高反应的效率. 该方法对各种官能团的容忍性好, 为从氯代烷烃出发直接合成查尔酮类化合物提供了一条新途径.

关键词: β-氯代烷基芳基酮, Heck反应, 烯酮, Domino反应, 查尔酮

Abstract:

A new method has been developed for the cross-coupling of aryl halides with β-chloroalkyl aryl ketones and their ester and amide analogs through a domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction sequence. The enone intermediates generated in situ reduced the occurrence of side reactions and therefore enhanced the efficiency of the reaction. This reaction exhibited good tolerance to various functional groups on both substrates and provides rapid access to a wide range of chalcone derivatives.

Key words: β-Chloroalkyl aryl ketone, Heck reaction, Enone, Domino reaction, Chalcone

郭腾龙, 姜权彬, 余立坤, 余正坤. 经由Domino脱HCl/Pd(OAc)₂催化的Heck反应合成查尔酮[J]. 催化学报, 2015, 36(1): 78-85.

Tenglong Guo, Quanbin Jiang, Likun Yu, Zhengkun Yu. Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction[J]. Chinese Journal of Catalysis, 2015, 36(1): 78-85.

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经由Domino脱HCl/Pd(OAc)₂催化的Heck反应合成查尔酮

Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction

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