Rhodium(III)-catalyzed Oxidative Coupling of N-Methoxybenzamides and Ethenesulfonyl fluoride: a C-H Bond Activation Strategy for the Preparation of 2-Aryl ethenesulfonyl fluorides and Sulfonyl fluoride Substituted γ-Lactams

被引：56

作者：

Wang, Shi-Meng ^{[1
]}

Li, Chen ^{[1
]}

Leng, Jing ^{[1
]}

Bukhari, Syed Nasir Abbas ^{[1
]}

Qin, Hua-Li ^{[1
]}

机构：

[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, 205 Luoshi Rd, Wuhan 430070, Hubei, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 09期

基金：

中国国家自然科学基金;

关键词：

PHENYLBORONIC ACID; CLICK CHEMISTRY; SCALE SYNTHESIS; SUFEX CLICK; OLEFINATION; RHODIUM; OXIDANT; ALKENES; 1,4-ADDITION; POLYSULFATES;

D O I：

10.1039/c7qo01128h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the synthesis of 2-aryl ethenesulfonyl fluorides and sulfonyl fluoride substituted gamma-lactams was developed through a rhodium(III)-catalyzed oxidative coupling of N-methoxybenzamides and ethenesulfonyl fluoride (ESF) in moderate to excellent yields. This protocol featured an exclusive E-stereo selectivity and a monoselective ortho activation of sp(2) C-H bonds of the phenyl rings. This research revealed that the much less reactive Heck coupling partner ethenesulfonyl fluoride (ESF) possesses the feasibility for coupling with sp(2) C-H bonds to provide a class of new sulfonyl fluoride scaffolds for the SuFEx click reaction.

引用

页码：1411 / 1415

页数：5

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