N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive, Electronically-Activated Amides in Catalytic N-C(O) Cleavage

被引：57

作者：

Meng, Guangrong ^{[1
]}

Lalancette, Roger ^{[1
]}

Szostak, Roman ^{[2
]}

Szostak, Michal ^{[1
]}

机构：

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

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

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 17期

关键词：

HETEROCYCLIC CARBENE COMPLEXES; CROSS-COUPLING REACTIONS; C BOND ACTIVATION; TWISTED AMIDES; SUZUKI-MIYAURA; NICKEL CATALYSIS; KETONE SYNTHESIS; GENERAL-METHOD; ESTERS; NHC;

D O I：

10.1021/acs.orglett.7b02288

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Despite recent progress in catalytic cross coupling technologies, the direct activation of N-alkyl-N-aryl amides has been a challenging transformation. Here, we report the first Suzuki cross-coupling of N-methylamino pyrimidyl amides (MAPA) enabled by the controlled n(N) -> pi(Ar), conjugation and the resulting remodeling of the partial double bond character of the amide bond. The new mode of amide activation is suitable for generating aryl-metal intermediates from unactivated primary and secondary amides.

引用

页码：4656 / 4659

页数：4

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