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Stereo‐ and Regioselective Cu‐Catalyzed Hydroboration of Alkynyl Chalcogenoethers

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A mild stereo‐ and regioselective Cu‐catalyzed hydroboration method for the synthesis of (Z)‐seleno‐alkenyl boronates and (Z)‐thio‐alkenylboronates from internal alkynes in the presence of commercially available B2pin2 is presented. This highly… Click to show full abstract

A mild stereo‐ and regioselective Cu‐catalyzed hydroboration method for the synthesis of (Z)‐seleno‐alkenyl boronates and (Z)‐thio‐alkenylboronates from internal alkynes in the presence of commercially available B2pin2 is presented. This highly selective transformation relies on the use of N‐heterocyclic carbene (NHC) complex IPrCuCl as the active catalytic species. We also explore the functionalization of the alkenylboronates obtained via oxidation to give α‐chalcogeno ketones, useful building blocks for the synthesis of more complex chalcogen‐containing molecules.

Keywords: regioselective catalyzed; stereo regioselective; alkynyl chalcogenoethers; hydroboration alkynyl; catalyzed hydroboration

Journal Title: ChemCatChem
Year Published: 2020

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