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Borazine‐CF 3 − Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation
Author(s) -
Geri Jacob B.,
Wade Wolfe Michael M.,
Szymczak Nathaniel K.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711316
Subject(s) - trifluoromethylation , electrophile , borazine , chemistry , nucleophile , reagent , yield (engineering) , photochemistry , adduct , catalysis , organic chemistry , combinatorial chemistry , inorganic chemistry , trifluoromethyl , materials science , alkyl , boron nitride , metallurgy
Abstract A fluoroform‐derived borazine CF 3 − transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C−H and C−X trifluoromethylation reactions. Mechanistic analysis supports a dissociative mechanism for CF 3 − transfer, and cation modification afforded a reagent with enhanced stability.