Copper-Mediated Difunctionalization of Alkenylboronic Acids: Synthesis of α-Imino Ketones

被引：9

作者：

Jiao, Ji-Wen ^{[1
,2
]}

Bi, Hong-Yan ^{[1
,2
]}

Zou, Pei-Sen ^{[1
,2
]}

Wang, Zhi-Xin ^{[1
,2
]}

Liang, Cui ^{[1
,2
]}

Mo, Dong-Liang ^{[1
,2
]}

机构：

[1] Guangxi Normal Univ, Minist Educ China, State Key Lab Chem & Mol Engn Med Resources, 15 Yu Cai Rd, Guilin 541004, Peoples R China

[2] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, 15 Yu Cai Rd, Guilin 541004, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 17期

基金：

中国国家自然科学基金;

关键词：

alkenylboronic acids; benzotriazolamines; copper-catalyzed; difunctionalization; alpha-imino ketones; ENANTIOSELECTIVE INTRAMOLECULAR AMINOOXYGENATION; SHARPLESS ASYMMETRIC AMINOHYDROXYLATION; CHEMOSELECTIVE N-ARYLATION; BORONIC ACIDS; CASCADE REACTIONS; OXIDATIVE DIFUNCTIONALIZATION; CONJUGATED DIENES; COUPLING REACTION; HYDROXAMIC ACIDS; DOMINO REACTIONS;

D O I：

10.1002/adsc.201800718

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Various alpha-imino ketones were prepared in good yields through a copper-mediated difunctionalization of alkenylboronic acids with benzotriazolamine in air. Mechanistic studies showed that alpha-imino ketones formation occurred through an initial copper-mediated coupling reaction to form an enamine, followed by homolysis of the C-Cu bond to produce an alpha-radical imine, and finally radical oxidation by air. The alpha-imino ketones were easily converted to various useful scaffolds through further transformations.

引用

页码：3254 / 3259

页数：6

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