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Ligand‐Promoted Oxidative Cross‐Coupling of Aryl Boronic Acids and Aryl Silanes by Palladium Catalysis
Author(s) -
Yu Jingxun,
Liu Jun,
Shi Guangfa,
Shao Changdong,
Zhang Yanghui
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201412288
Subject(s) - chemistry , aryl , silanes , nucleophile , palladium , ligand (biochemistry) , binap , reagent , oxidative addition , combinatorial chemistry , organic chemistry , coupling reaction , catalysis , selectivity , medicinal chemistry , enantioselective synthesis , silane , biochemistry , alkyl , receptor
The first cross‐coupling reaction between aryl silanes and aryl boronic acids is described. This transformation represents one of the very few examples of coupling reactions between two nucleophilic organometallic reagents and provides a new method for the formation of biaryl compounds. The successful development of this reaction was enabled by the use of commercially available 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) as the ligand. A small amount of BINAP (3 mol %) was sufficient to suppress the formation of the homocoupling products, and the reaction yielded the cross‐coupling products with high selectivity under mild conditions, even when the ratio of the two coupling partners was 1:1.