Open AccessEfficient Difluoromethylation of sp 3 Carbon Nucleophiles by Bromodifluoromethylation Reagents with Organic Bases
Author(s) -
Liu Guokai,
Wang Xin,
Lu Xu,
Xu XiuHua,
Tokunaga Etsuko,
Shibata Norio
Publication year - 2012
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201200033
Subject(s) - nucleophile , reagent , chemistry , electrophile , base (topology) , organic synthesis , allylic rearrangement , organic chemistry , carbon fibers , combinatorial chemistry , organic base , catalysis , computer science , mathematics , mathematical analysis , algorithm , composite number
Bromodifluoromethylation reagents 1 can be used during electrophilic difluoromethylation for sp 3 carbon nucleophiles mediated by organic bases. Allylic difluoromethylation of dicyanoalkylidens proceeds nicely by 1 in the presence of P 1 base to give CF 2 H instead of CF 2 Br products in high to excellent yields. A wide range of β‐ketoesters are also efficiently reacted with 1 , mediated by DBU to provide CCF 2 H compounds as major products with a small amount of OCF 2 H products in high to excellent yields.