Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes

A transition metal free process for conjunctive functionalization of alkenylboron ate-complexes with electrophilic fluoroalkylthiolating reagents is described, affording β-trifluoroalkylthiolated and difluoroalkylthiolated boronic esters in good yield and excellent diastereoselectivity. The potentia...

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Detalles Bibliográficos
Autores principales: Shen, Feng, Lu, Long, Shen, Qilong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163329/
https://www.ncbi.nlm.nih.gov/pubmed/34123079
http://dx.doi.org/10.1039/d0sc03039b
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author Shen, Feng
Lu, Long
Shen, Qilong
author_facet Shen, Feng
Lu, Long
Shen, Qilong
author_sort Shen, Feng
collection PubMed
description A transition metal free process for conjunctive functionalization of alkenylboron ate-complexes with electrophilic fluoroalkylthiolating reagents is described, affording β-trifluoroalkylthiolated and difluoroalkylthiolated boronic esters in good yield and excellent diastereoselectivity. The potential applicability of the method was demonstrated by the preparation of a difluoromethylthiolated mimic 12 of a potential drug molecule PF-4191834 for the treatment of asthma.
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spelling pubmed-81633292021-06-11 Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes Shen, Feng Lu, Long Shen, Qilong Chem Sci Chemistry A transition metal free process for conjunctive functionalization of alkenylboron ate-complexes with electrophilic fluoroalkylthiolating reagents is described, affording β-trifluoroalkylthiolated and difluoroalkylthiolated boronic esters in good yield and excellent diastereoselectivity. The potential applicability of the method was demonstrated by the preparation of a difluoromethylthiolated mimic 12 of a potential drug molecule PF-4191834 for the treatment of asthma. The Royal Society of Chemistry 2020-07-07 /pmc/articles/PMC8163329/ /pubmed/34123079 http://dx.doi.org/10.1039/d0sc03039b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Shen, Feng
Lu, Long
Shen, Qilong
Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
title Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
title_full Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
title_fullStr Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
title_full_unstemmed Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
title_short Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
title_sort electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163329/
https://www.ncbi.nlm.nih.gov/pubmed/34123079
http://dx.doi.org/10.1039/d0sc03039b
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AT lulong electrophilicfluoroalkylthiolationinduceddiastereoselectiveandstereospecific12metalatemigrationofalkenylboronatecomplexes
AT shenqilong electrophilicfluoroalkylthiolationinduceddiastereoselectiveandstereospecific12metalatemigrationofalkenylboronatecomplexes

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