General Method for the Suzuki Miyaura Cross-Coupling of Amides Using Commercially Available, Air-and Moisture-Stable Palladium/ NHC (NHC = N-Heterocyclic Carbene) Complexes

被引：167

作者：

Lei, Peng ^{[1
,2
]}

Meng, Guangrong ^{[1
]}

Szostak, Michal ^{[1
]}

机构：

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

[2] China Agr Univ, Coll Sci, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

ACS CATALYSIS | 2017年 / 7卷 / 03期

关键词：

palladium; N-heterocyclic carbenes (NHCs); N-C activation; Suzuki Miyaura cross-coupling; amides; ARYL CHLORIDES; TWISTED AMIDES; BOND-CLEAVAGE; CATALYZED ACTIVATION; BUCHWALD-HARTWIG; KETONE SYNTHESIS; C CLEAVAGE; NITROGEN; REAGENTS; LIGANDS;

D O I：

10.1021/acscatal.6b03616

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The direct Suzuki Miyaura cross-coupling of amides catalyzed by Pd-NHC complexes is reported. Using a single protocol, commercially available, air-and moisture stable (NHC)Pd(R-allyl)Cl complexes can effect Suzuki Miyaura cross-coupling of a wide range of amides with arylboronic acids in very good yields. The studies described herein represent the use of versatile Pd-NHC complexes as catalysts for transition-metal-catalyzed cross-coupling of amides by N-C bond activation. The Pd-NHC catalysts provide a significant improvement over all current Pd-PR3 systems employed for the amide N -C bond activation. Mechanistic studies provide strong support for the development of a unified reactivity scale of the amide bond for the generation of aryl-metal intermediates.

引用

页码：1960 / 1965

页数：6

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