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Enantiospecific Trifluoromethyl‐Radical‐Induced Three‐Component Coupling of Boronic Esters with Furans
Author(s) -
Wang Yahui,
Noble Adam,
Sandford Christopher,
Aggarwal Varinder K.
Publication year - 2017
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.201611058
Subject(s) - trifluoromethyl , furan , chemistry , electrophile , reagent , aryl , alkyl , component (thermodynamics) , coupling (piping) , boronic acid , medicinal chemistry , coupling reaction , organic chemistry , combinatorial chemistry , catalysis , mechanical engineering , physics , engineering , thermodynamics
In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2‐lithio furan and non‐racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three‐component coupling to give the corresponding 2,5‐disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2‐metallate rearrangement upon single‐electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three‐component coupling reactions.