title: A reagent for the one-step preparation of potassium acyltrifluoroborates (KATs) from aryl- and heteroarylhalides.
abstract: 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 nBuLi 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.
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Bioscience, ETH Zürich, 8093 Zürich (Switzerland) http://www.bode.ethz.ch.
authors.forename: Gábor
authors.initials: G
authors.lastname: Erős
authors.forename: Yo
authors.initials: Y
authors.lastname: Kushida
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode
keywords: arenes; boron; lithiation; synthetic methods; zwitterions