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Catalytic Synthesis of Potassium Acyltrifluoroborates (KATs) through Chemoselective Cross‐Coupling with a Bifunctional Reagent
Author(s) -
Wu Dino,
Fohn Nicole A.,
Bode Jeffrey W.
Publication year - 2019
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.201904576
Subject(s) - bifunctional , reagent , potassium , catalysis , chemistry , coupling (piping) , combinatorial chemistry , organic chemistry , materials science , metallurgy
Potassium acyltrifluoroborates (KATs) are increasingly important functional groups, and general methods for their preparation are of great current interest. We report a bifunctional iminium reagent bearing both a tin nucleophile and a trifluoroborate, which was applied in chemoselective Pd 0 ‐catalyzed Migita–Kosugi–Stille cross‐coupling reactions owith aryl and vinyl halides. This method gives access to previously inaccessible aromatic and α,β‐unsaturated acyltrifluoroborates, including precursors to amino‐acid derived KATs.