A Reagent for the One‐Step Preparation of Potassium Acyltrifluoroborates (KATs) from Aryl‐ and Heteroarylhalides1. Issue 29 (30th May 2014)

• Record Type: Journal Article
• Authors: Erős, Gábor; Kushida, Yo; Bode, Jeffrey W.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 29(2014)
• Page Start: 7604
• Page End: 7607
• Publication Date: 2014-05-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201403931
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>n</italic>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.</p> </abstract>