期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 14, 页码 7305-7310出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01077
关键词
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资金
- American Chemical Society Petroleum Research Fund [52706-UNI1]
- Smith College
- McKinley Fellowship
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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