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A Reagent for the One‐Step Preparation of Potassium Acyltrifluoroborates (KATs) from Aryl‐ and Heteroarylhalides
Author(s) -
Erős Gábor,
Kushida Yo,
Bode Jeffrey W.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403931
Subject(s) - reagent , aryl , halide , chemistry , potassium , alkylation , zwitterion , nitro , organic chemistry , combinatorial chemistry , molecule , catalysis , alkyl
Potassium acyltrifluoroborates (KATs) are fascinating functional groups whose further exploration is limited by poor synthetic access. Documented herein is the design and synthesis of a new reagent for their one‐step preparation from aryl‐ and heteroarylhalides. The reagent is a stable, soluble zwitterion prepared by S‐alkylation of a novel thioformamide trifluoroboronate. The KATs are prepared by adding one equivalent of n BuLi to a mixture of the aryl halide and the reagent at −78 °C. This protocol is suitable for the preparation of KATs containing pyridines, esters, nitro groups, and halides.