Unexpected Phenol Production from Arylboronic Acids under Palladium-Free Conditions; Organocatalyzed Air Oxidation

被引：34

作者：

Cammidge, Andrew N. ^{[1
]}

Goddard, Victoria H. M. ^{[1
]}

Schubert, Christopher P. J. ^{[1
]}

Gopee, Hemant ^{[1
]}

Hughes, David L. ^{[1
]}

Gonzalez-Lucas, Daniel ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem, Norwich NR4 7TJ, Norfolk, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 22期

基金：

英国工程与自然科学研究理事会;

关键词：

CROSS-COUPLING REACTION; CARBON BOND FORMATION; ORGANOBORON COMPOUNDS; PHENYLBORONIC ACID; HIGHLY EFFICIENT; HYDROXYLATION; COMPLEXES; CATALYSIS; DIOXYGEN; BIARYLS;

D O I：

10.1021/ol202500z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intriguing class of quinones that efficiently catalyze the air oxidation (overall hydroxylation) of arylboronic acids to the corresponding phenol is reported. Autocatalysis In the parent system Is particularly efficient and leads to rapid, quantitative synthesis of quinones such as 4 from boronic acid 1 at room temperature using air as stoichlometric oxidant. The efficiency results from a balance between two-stage conjugate addition and migration with each step driven by aromatization of a naphthalene fragment.

引用

页码：6034 / 6037

页数：4

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