Stereo- and regioselective cu-catalyzed hydroboration of alkynyl chalcogenoethers

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 a -chalcogeno ketones, useful building blocks for the synthesis of more complex chalcogen-containing molecules.
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alkynyl selenides;  alkenylboronates;  hydroboration;  NHC ligands;  thioacetylenes

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Oliveira IM., Esteves HA., Darbem MP., Sartorelli A, Correra TC., Rodrigues-Oliveira AF., et al. Stereo- and regioselective cu-catalyzed hydroboration of alkynyl chalcogenoethers. ChemCatChem. 2020 May. doi:10.1002/cctc.202000395.
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