Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid

被引：26

作者：

Jacobson, Clare E. ^{[1
]}

Martinez-Munoz, Noelia ^{[1
]}

Gorin, David J. ^{[1
]}

机构：

[1] Smith Coll, Dept Chem, Northampton, MA 01063 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 14期

关键词：

CARBOXYLIC-ACIDS; BORONIC ACIDS; H BONDS; ARYLATION; ESTERS; PHENOLS; ALDEHYDES; ALCOHOLS; AMIDES; ESTERIFICATION;

D O I：

10.1021/acs.joc.5b01077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidative coupling of alkylboronic acids with oxygen nucleophiles offers a strategy for replacing toxic, electrophilic alkylating reagents. Although the Chan-Lam reaction has been widely applied in the arylation of heteroatom nudeophiles, O-alkylation with boronic acids is rare. We report a Cu-catalyzed nondecarboxylative methylation of carboxylic acids with methylboronic acid that proceeds in air with no additional oxidant. An isotope-labeling study supports an oxidative cross-coupling mechanism, in analogy to that proposed for Chan-Lam arylation.

引用

页码：7305 / 7310

页数：6

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