Transition Metal-Free Regio- and Stereo-Selective trans Hydroboration of 1,3-Diynes: A Phosphine-Catalyzed Access to (E)-1-Boryl-1,3-Enynes.
enediyne
enyne
hydroboration
organocatalytic
stereoselective
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
11 Nov 2022
11 Nov 2022
Historique:
received:
28
07
2022
pubmed:
3
8
2022
medline:
3
8
2022
entrez:
2
8
2022
Statut:
ppublish
Résumé
We report a transition metal-free, regio- and stereo-selective, phosphine-catalyzed method for the trans hydroboration of 1,3-diynes with pinacolborane that affords (E)-1-boryl-1,3-enynes. The reaction proceeds with excellent selectivity for boron addition to the external carbon of the 1,3-diyne framework as unambiguously established by NMR and X-ray crystallographic studies. The reaction displays a broad substrate scope including unsymmetrical diynes to generate products in high yield (up to 95 %). Experimental and theoretical studies suggest that phosphine attack on the alkyne is a key process in the catalytic cycle.
Identifiants
pubmed: 35917135
doi: 10.1002/chem.202202349
pmc: PMC9804376
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202202349Subventions
Organisme : National Science Foundation
ID : CHE-1726077
Organisme : Reseach Grants Council of Hong Kong
ID : HKUST16300021
Organisme : Julius-Maximilians-Universität Würzburg
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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