Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

被引：30

作者：

Wang, Mei-Ling ^{[1
]}

Xu, Hui ^{[2
]}

Li, Han-Yuan ^{[2
]}

Ma, Biao ^{[2
]}

Wang, Zhen-Yu ^{[3
]}

Wang, Xing ^{[2
]}

Dai, Hui-Xiong ^{[2
,4
]}

机构：

[1] Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Jiangsu, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China

[3] Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Jiangsu, Peoples R China

[4] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 06期

基金：

中国国家自然科学基金;

关键词：

CATALYZED HECK; PALLADIUM; CHLORIDES; ARYLATION; CLEAVAGE;

D O I：

10.1021/acs.orglett.1c00296

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

引用

页码：2147 / 2152

页数：6

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