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

被引：28
|
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
收藏
页码：2147 / 2152
页数：6
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