在含水介质中钯高效催化咪唑并[1,2-a]吡啶类化合物与芳基氯代物的碳氢芳基化反应

doi:10.6023/cjoc201710029

有机化学 ›› 2018, Vol. 38 ›› Issue (1): 95-102.DOI: 10.6023/cjoc201710029 上一篇下一篇

所属专题：庆祝吴养洁院士九十华诞专辑；碳氢活化合辑2018-2019

研究论文

在含水介质中钯高效催化咪唑并[1,2-a]吡啶类化合物与芳基氯代物的碳氢芳基化反应

穆兵^a,b, 李敬亚^d, 邹大鹏^c, 吴豫生^c,d, 常俊标^a,c, 吴养洁^c

a 郑州大学药学院郑州 450001;
b 郑州师范学院化学化工学院郑州 450044;
c 郑州大学化学与分子工程学院郑州 450001;
d 郑州泰基鸿诺医药股份有限公司郑州 450001

收稿日期:2017-10-24 修回日期:2017-11-27 发布日期:2017-11-28
通讯作者: 吴豫生, 常俊标, 吴养洁 E-mail:yusheng.wu@tetranovglobal.com;changjunbiao@zzu.edu.cn;wyj@zzu.edu.cn
基金资助:
国家自然科学基金（No.21702191）、河南省科技攻关项目（No.172102210555）和河南省博士后科研（No.2014003）资助项目.

Efficient Pd-Catalyzed Direct C-H Bond Arylation of Imidazo-[1, 2-a]pyridines with Aryl Chlorides in Aqueous Medium

Mu Bing^a,b, Li Jingya^d, Zou Dapeng^c, Wu Yusheng^c,d, Chang Junbiao^a,c, Wu Yangjie^c

a School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001;
b College of Chemistry and Chemical Engineering, Zhengzhou Normal University, Zhengzhou 450044;
c College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
d Tetranov Biopharm, LLC, Zhengzhou 450001

Received:2017-10-24 Revised:2017-11-27 Published:2017-11-28
Contact: 10.6023/cjoc201710029 E-mail:yusheng.wu@tetranovglobal.com;changjunbiao@zzu.edu.cn;wyj@zzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21702191), the Scientific and Technological Project of Henan Province (No. 172102210555) and the Postdoctoral Science Foundation of Henan Province (No. 2014003).

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1. 在含水介质中钯高效催化咪唑并[1,2-a]吡啶类化合物与芳基氯代物的碳氢芳基化反应.PDF(1350KB)

摘要/Abstract

3-芳基咪唑并[1，2-a]吡啶骨架广泛存在于药物结构中，在药物学方面具有重要的地位及在材料化学、有机化学等方面也具有潜在的应用价值.在含水介质中，利用醋酸钯催化咪唑并[1，2-a]吡啶及其衍生物与芳基/杂芳基氯代物的碳氢芳基化反应，简便、高效地合成系列3-芳基咪唑并[1，2-a]吡啶类化合物，并以较好至优秀的收率获得芳基化产品.该方法采用廉价易得的芳基/杂芳基氯代物和咪唑并[1，2-a]吡啶类化合物为偶联反应的底物，且底物的范围能够拓展至缺电子、富电子的芳基氯代物和杂芳基氯代物及多种基团取代的咪唑并[1，2-a]吡啶类化合物.

关键词: 碳氢芳基化, 咪唑并[1,2-a]吡啶, 3-芳基咪唑并[1,2-a]吡啶, 芳基/杂芳基氯代物, 含水介质

An efficient and practical protocol for palladium-catalyzed direct C—H bond arylation of imidazo[1,2-a]pyridines with cheap aryl/heteroaryl chlorides has been developed. Various imidazo[1,2-a]pyridines with electron-neutral, electron-poor, electron-rich, even sterically hindered aryl chlorides and heteroaryl chlorides were successfully applied to the reaction in aqueous medium to achieve the 3-arylimidazo[1,2-a]pyridines in mostly good to excellent yields, thus representing a signi?- cant advancement in the implementation of the direct C—H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides.

Key words: C-H bond arylation, imidazo[1,2-a]pyridines, 3-arylimidazo[1,2-a]pyridines, aryl/heteroaryl chlorides, aqueous medium

引用此文

穆兵, 李敬亚, 邹大鹏, 吴豫生, 常俊标, 吴养洁. 在含水介质中钯高效催化咪唑并[1,2-a]吡啶类化合物与芳基氯代物的碳氢芳基化反应[J]. 有机化学, 2018, 38(1): 95-102.

Mu Bing, Li Jingya, Zou Dapeng, Wu Yusheng, Chang Junbiao, Wu Yangjie. Efficient Pd-Catalyzed Direct C-H Bond Arylation of Imidazo-[1, 2-a]pyridines with Aryl Chlorides in Aqueous Medium[J]. Chin. J. Org. Chem., 2018, 38(1): 95-102.

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在含水介质中钯高效催化咪唑并[1,2-a]吡啶类化合物与芳基氯代物的碳氢芳基化反应

Efficient Pd-Catalyzed Direct C-H Bond Arylation of Imidazo-[1, 2-a]pyridines with Aryl Chlorides in Aqueous Medium

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