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
收藏
页码：1434 / 1437
页数：4
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