Practical C-H Functionalization of Quinones with Boronic Acids

被引：314

作者：

Fujiwara, Yuta ^{[1
]}

Domingo, Victoriano ^{[1
]}

Seiple, Ian B. ^{[1
]}

Gianatassio, Ryan ^{[1
]}

Del Bel, Matthew ^{[1
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem & Chem Biol, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 10期

基金：

日本学术振兴会;

关键词：

ARYLBORONIC ACIDS; REDUCTIVE ALKYLATION; RADICAL REACTIONS; ARYLATION; TRIALKYLBORANES; KINAMYCINS; ACETATE; 1,4-NAPHTHOQUINONES; BIOSYNTHESIS; INHIBITORS;

D O I：

10.1021/ja111152z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct functionalization of a variety of quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver-(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl-and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone. This method has been applied to complex substrates, including a steroid derivative and a farnesyl natural product.

引用

页码：3292 / 3295

页数：4

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