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Stereo‐ and Regioselective Cu‐Catalyzed Hydroboration of Alkynyl Chalcogenoethers
Author(s) -
Oliveira Isadora M.,
Esteves Henrique A.,
Darbem Mariana P.,
Sartorelli Arthur,
Correra Thiago C.,
RodriguesOliveira André F.,
Pimenta Daniel C.,
ZukermanSchpector Julio,
Manarin Flávia,
Stefani Hélio A.
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000395
Subject(s) - hydroboration , regioselectivity , chemistry , catalysis , thio , carbene , surface modification , combinatorial chemistry , organic chemistry , stereochemistry
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 B 2 pin 2 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.