Catalytic Synthesis of Potassium Acyltrifluoroborates (KATs) through Chemoselective Cross‐Coupling with a Bifunctional Reagent. Issue 32 (3rd July 2019)

• Record Type: Journal Article
• Authors: Wu, Dino; Fohn, Nicole A.; Bode, Jeffrey W.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 32(2019)
• Page Start: 11058
• Page End: 11062
• Publication Date: 2019-07-03
• Subjects: acylboron compounds -- cross-coupling -- Stille reactions -- synthetic methods -- zwitterions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201904576
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : The adventures of tin‐TIM : A trifluoroborate iminium (TIM) bearing a tin moiety undergoes palladium catalyzed cross‐coupling to provide potassium acyltrifluoroborates (KATs) in good yields under mild reaction conditions. This approach provides access to aryl and unsaturated KATs, including amino acid precursors.