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.
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收藏
页码：7305 / 7310
页数：6
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