Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group

被引：78

作者：

Liu, Chengwei ^{[1
]}

Liu, Yongmei ^{[1
,2
]}

Liu, Ruzhang ^{[2
]}

Lalancette, Roger ^{[1
]}

Szostak, Roman ^{[3
]}

Szostak, Michal ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA

[2] Yangzhou Univ, Coll Chem & Chem Engn, 180 Siwangting Rd, Yangzhou 225002, Jiangsu, Peoples R China

[3] Univ Wroclaw, Dept Chem, F Joliot Curie 14, PL-50383 Wroclaw, Poland

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 06期

基金：

中国国家自然科学基金;

关键词：

NITROGEN BOND-CLEAVAGE; ARYL MESYLATES; NICKEL CATALYSIS; TWISTED AMIDES; KETONE SYNTHESIS; ACTIVATION; ACYLSACCHARINS; ESTERS; FUNCTIONALIZATION; MONOARYLATION;

D O I：

10.1021/acs.orglett.7b00373

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general Pd-catalyzed Suzuki-Miyaura cross-coupling of N-mesylamides with arylboronic acids by selective N-C cleavage has been developed. The presented results represent the first example of a transition-metal-catalyzed cross-coupling of amides activated by an atom-economic, cheap, and benign mesyl group. The reaction delivers arylated products featuring a range of useful functional groups by chemoselective cleavage of the amide N-C bond with high efficiency. Both the scope and the origin of high selectivity are discussed. A beneficial effect of the N-mesyl substituent on the bond activation in acyclic amides is presented.

引用

页码：1434 / 1437

页数：4

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