Pd-Catalyzed Semmler-Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines

被引：123

作者：

Hong, Wan Pyo ^{[1
]}

Iosub, Andrei V. ^{[1
]}

Stahl, Shannon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 37期

基金：

美国国家科学基金会;

关键词：

KETONE O-PENTAFLUOROBENZOYLOXIMES; AEROBIC DEHYDROGENATION; ARYL CHLORIDES; AROMATIC-AMINES; AMINATION; AMMONIA; CYCLIZATION; ARYLATION; CYCLOHEXANONES; DERIVATIVES;

D O I：

10.1021/ja4073172

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.

引用

页码：13664 / 13667

页数：4

共 41 条

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