Transition-Metal-Free Esterification of Amides via Selective N-C Cleavage under Mild Conditions

被引：91
|
作者：
Li, Guangchen [1 ]
Lei, Peng [1 ,2 ]
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：
ORGANIC LETTERS | 2018年 / 20卷 / 18期
关键词：
CATALYZED ESTERIFICATION; NICKEL CATALYSIS; TWISTED AMIDES; ARYL ESTERS; DESTABILIZATION; DECARBONYLATION; RELEVANCE; ROTATION;
D O I：
10.1021/acs.orglett.8b02323
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general, transition-metal-free, and operationally simple method for esterification of amides by a highly selective cleavage of N-C(O) bonds under exceedingly mild conditions is reported. The reaction is characterized by broad substrate scope and excellent functional group tolerance. The potential of this mild esterification is highlighted by late-stage diversification of natural products and pharmaceuticals. Conceptually, the metal-free acyl functionalization of amides represents a significant step forward as a practical alternative to ligand exchange in acylmetal intermediates.
引用
收藏
页码：5622 / 5625
页数：4
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