Aminoquinoline-assisted vinylic C-H arylation of unsubstituted acrylamide for the selective synthesis of Z olefins

被引：25

作者：

Cheng, Xiuzhi ^{[1
]}

Chen, Zhen ^{[1
]}

Gao, Yadong ^{[1
]}

Xue, Fengtian ^{[2
]}

Jiang, Chao ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Dept Pharmaceut Engn, Nanjing 210094, Jiangsu, Peoples R China

[2] Univ Maryland, Sch Pharm, Dept Pharmaceut Sci, 20 Penn St, Baltimore, MD 21201 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 12期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM-CATALYZED ARYLATION; UNACTIVATED C(SP(3))-H BONDS; STEREOSELECTIVE-SYNTHESIS; ORTHO-C(SP(2))-H BONDS; DIRECTED ALKYLATION; EFFICIENT SYNTHESIS; ACID DERIVATIVES; Z-ALKENES; FUNCTIONALIZATION; ACTIVATION;

D O I：

10.1039/c6ob00164e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for Pd-catalyzed, aminoquinoline-directed arylation of vinylic C-H bonds with aryl iodides has been developed. This reaction represents a rare example of Pd-catalyzed vinylic C-H functionalization of unsubstituted acrylamide, allowing for the highly regio-and stereoselective preparation of Z-olefins. High tolerance to functional groups is observed with good yields and excellent selectivity. It offers a complementary synthetic method to traditional pathways for Z-olefins.

引用

页码：3298 / 3306

页数：9

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