Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction

[Image: see text] A highly diastereoselective Pd(0)-catalyzed Mizoroki–Heck reaction of gem-difluoroalkenes is described. Unlike previously reported C–F bond functionalization with organometallic reagents, this reaction takes place between two different alkenes to achieve a formal C–F and C–H bond c...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Yanhui, Tsui, Gavin Chit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10463225/
https://www.ncbi.nlm.nih.gov/pubmed/37584488
http://dx.doi.org/10.1021/acs.orglett.3c02452
_version_ 1785098183514259456
author Wang, Yanhui
Tsui, Gavin Chit
author_facet Wang, Yanhui
Tsui, Gavin Chit
author_sort Wang, Yanhui
collection PubMed
description [Image: see text] A highly diastereoselective Pd(0)-catalyzed Mizoroki–Heck reaction of gem-difluoroalkenes is described. Unlike previously reported C–F bond functionalization with organometallic reagents, this reaction takes place between two different alkenes to achieve a formal C–F and C–H bond cross-coupling via a distinct pathway. Monofluorinated 1,3-diene products can be synthesized with control of the geometry of each alkene and good functional group tolerability.
format Online
Article
Text
id pubmed-10463225
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-104632252023-08-30 Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction Wang, Yanhui Tsui, Gavin Chit Org Lett [Image: see text] A highly diastereoselective Pd(0)-catalyzed Mizoroki–Heck reaction of gem-difluoroalkenes is described. Unlike previously reported C–F bond functionalization with organometallic reagents, this reaction takes place between two different alkenes to achieve a formal C–F and C–H bond cross-coupling via a distinct pathway. Monofluorinated 1,3-diene products can be synthesized with control of the geometry of each alkene and good functional group tolerability. American Chemical Society 2023-08-16 /pmc/articles/PMC10463225/ /pubmed/37584488 http://dx.doi.org/10.1021/acs.orglett.3c02452 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Wang, Yanhui
Tsui, Gavin Chit
Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction
title Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction
title_full Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction
title_fullStr Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction
title_full_unstemmed Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction
title_short Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction
title_sort stereoselective palladium-catalyzed c–f bond alkenylation of tetrasubstituted gem-difluoroalkenes via mizoroki–heck reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10463225/
https://www.ncbi.nlm.nih.gov/pubmed/37584488
http://dx.doi.org/10.1021/acs.orglett.3c02452
work_keys_str_mv AT wangyanhui stereoselectivepalladiumcatalyzedcfbondalkenylationoftetrasubstitutedgemdifluoroalkenesviamizorokiheckreaction
AT tsuigavinchit stereoselectivepalladiumcatalyzedcfbondalkenylationoftetrasubstitutedgemdifluoroalkenesviamizorokiheckreaction

Ejemplares similares