Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization

被引：55

作者：

Chen, Yifeng ^{[1
]}

Huang, David ^{[1
]}

Zhao, Yizhou ^{[1
]}

Newhouse, Timothy R. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, 225 Prospect St,POB 208107, New Haven, CT 06511 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 28期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

dehydrogenation; natural products; palladium; synthetic methods; vicinal difunctionalization; DIRECT BETA-ARYLATION; CARBONYL-COMPOUNDS; FUNCTIONALIZATION; ESTERS; ALPHA; BETA-DEHYDROGENATION; PHOTOREDOX; ALDEHYDES; DESIGN;

D O I：

10.1002/anie.201704874

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The telescoping of allyl-palladium catalyzed ketone dehydrogenation with organocuprate conjugate addition chemistry allows for the introduction of aryl, heteroaryl, vinyl, acyl, methyl, and other functionalized alkyl groups chemoselectively to a wide variety of unactivated ketone compounds via their enone counterparts. The compatibility of the dehydrogenation conditions additionally allows for efficient trapping of the intermediate enolate with various electrophiles. The utility of this approach is demonstrated by comparison to several previously reported multistep sequences.

引用

页码：8258 / 8262

页数：5

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