Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates

[Image: see text] Selective defluoroborylation and asymmetric hydroboration reactions of fluoroalkyl-substituted terminal alkenes with pinacolborane (HBpin) have been developed with cobalt catalysts generated from Co(acac)(2) and bisphosphine ligands. A variety of fluoroalkyl-substituted terminal al...

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Autores principales: Hu, Ming, Tan, Boon Beng, Ge, Shaozhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9434995/
https://www.ncbi.nlm.nih.gov/pubmed/35953077
http://dx.doi.org/10.1021/jacs.2c06488
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author Hu, Ming
Tan, Boon Beng
Ge, Shaozhong
author_facet Hu, Ming
Tan, Boon Beng
Ge, Shaozhong
author_sort Hu, Ming
collection PubMed
description [Image: see text] Selective defluoroborylation and asymmetric hydroboration reactions of fluoroalkyl-substituted terminal alkenes with pinacolborane (HBpin) have been developed with cobalt catalysts generated from Co(acac)(2) and bisphosphine ligands. A variety of fluoroalkyl-substituted terminal alkenes undergo this enantioselective hydroboration, affording the corresponding chiral alkylboronates containing fluoroalkyl-substituted stereogenic carbon centers with high enantioselectivity (up to 98% ee). This asymmetric hydroboration provides a versatile foundation for the synthesis of a variety of chiral organofluorine compounds containing fluoroalkyl-substituted stereogenic carbon centers.
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spelling pubmed-94349952022-09-02 Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates Hu, Ming Tan, Boon Beng Ge, Shaozhong J Am Chem Soc [Image: see text] Selective defluoroborylation and asymmetric hydroboration reactions of fluoroalkyl-substituted terminal alkenes with pinacolborane (HBpin) have been developed with cobalt catalysts generated from Co(acac)(2) and bisphosphine ligands. A variety of fluoroalkyl-substituted terminal alkenes undergo this enantioselective hydroboration, affording the corresponding chiral alkylboronates containing fluoroalkyl-substituted stereogenic carbon centers with high enantioselectivity (up to 98% ee). This asymmetric hydroboration provides a versatile foundation for the synthesis of a variety of chiral organofluorine compounds containing fluoroalkyl-substituted stereogenic carbon centers. American Chemical Society 2022-08-11 2022-08-24 /pmc/articles/PMC9434995/ /pubmed/35953077 http://dx.doi.org/10.1021/jacs.2c06488 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Hu, Ming
Tan, Boon Beng
Ge, Shaozhong
Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates
title Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates
title_full Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates
title_fullStr Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates
title_full_unstemmed Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates
title_short Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates
title_sort enantioselective cobalt-catalyzed hydroboration of fluoroalkyl-substituted alkenes to access chiral fluoroalkylboronates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9434995/
https://www.ncbi.nlm.nih.gov/pubmed/35953077
http://dx.doi.org/10.1021/jacs.2c06488
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AT tanboonbeng enantioselectivecobaltcatalyzedhydroborationoffluoroalkylsubstitutedalkenestoaccesschiralfluoroalkylboronates
AT geshaozhong enantioselectivecobaltcatalyzedhydroborationoffluoroalkylsubstitutedalkenestoaccesschiralfluoroalkylboronates

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