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Palladium‐Catalyzed Difluoroalkylation of Aryl Boronic Acids: A New Method for the Synthesis of Aryldifluoromethylated Phosphonates and Carboxylic Acid Derivatives
Author(s) -
Feng Zhang,
Min QiaoQiao,
Xiao YuLan,
Zhang Bo,
Zhang Xingang
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201309535
Subject(s) - aryl , palladium , catalysis , boronic acid , chemistry , combinatorial chemistry , catalytic cycle , organic chemistry , alkyl
The palladium‐catalyzed difluoroalkylation of aryl boronic acids with bromodifluoromethylphosphonate, bromodifluoroacetate, and further derivatives has been developed. This method provides a facile and useful access to a series of functionalized difluoromethylated arenes (ArCF 2 PO(OEt) 2 , ArCF 2 CO 2 Et, and ArCF 2 CONR 1 R 2 ) that have important applications in drug discovery and development. Preliminary mechanistic studies reveal that a single electron transfer (SET) pathway may be involved in the catalytic cycle.