Development of a Nickel-Catalyzed N-N Coupling for the Synthesis of Hydrazides

被引：25

作者：

Barbor, Jay P. ^{[1
]}

Nair, Vaishnavi N. ^{[1
]}

Sharp, Kimberly R. ^{[1
]}

Lohrey, Trevor D. ^{[1
]}

Dibrell, Sara E. ^{[1
]}

Shah, Tejas K. K. ^{[2
]}

Walsh, Martin J. ^{[2
]}

Reisman, Sarah E. ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

[2] Corteva Agrisci, Indianapolis, IN 46268 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 28期

关键词：

NIH CATALYSIS; NITROGEN; HYDROAMIDATION; LIGAND; OXYGEN;

D O I：

10.1021/jacs.3c04834

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nickel-catalyzedN-N cross-coupling for thesynthesisof hydrazides is reported. O-Benzoylated hydroxamateswere efficiently coupled with a broad range of aryl and aliphaticamines via nickel catalysis to form hydrazides in an up to 81% yield.Experimental evidence implicates the intermediacy of electrophilicNi-stabilized acyl nitrenoids and the formation of a Ni(I) catalystvia silane-mediated reduction. This report constitutes the first exampleof an intermolecular N-N coupling compatible with secondaryaliphatic amines.

引用

页码：15071 / 15077

页数：7

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