Cargando…

Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water

Visible-light-promoted site-selective and direct C–F bond functionalization of polyfluorinated iminosulfides was accomplished with alkenes and water under redox-neutral conditions, affording a diverse array of γ-lactams with a fluoro- and perfluoroalkyl-substituted carbon centre. A variety of perflu...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Tao, Zong, Yuan-Yuan, Huang, Tao, Jin, Xiao-Ling, Wu, Li-Zhu, Liu, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10599478/
https://www.ncbi.nlm.nih.gov/pubmed/37886085
http://dx.doi.org/10.1039/d3sc03771a
_version_ 1785125773957398528
author Wang, Tao
Zong, Yuan-Yuan
Huang, Tao
Jin, Xiao-Ling
Wu, Li-Zhu
Liu, Qiang
author_facet Wang, Tao
Zong, Yuan-Yuan
Huang, Tao
Jin, Xiao-Ling
Wu, Li-Zhu
Liu, Qiang
author_sort Wang, Tao
collection PubMed
description Visible-light-promoted site-selective and direct C–F bond functionalization of polyfluorinated iminosulfides was accomplished with alkenes and water under redox-neutral conditions, affording a diverse array of γ-lactams with a fluoro- and perfluoroalkyl-substituted carbon centre. A variety of perfluoroalkyl units, including C(2)F(5), C(3)F(7), C(4)F(9), and C(5)F(11) underwent site-selective defluorofunctionalization. This protocol allows high chemoselectivity control and shows excellent functional group tolerance. Mechanistic studies reveal that the remarkable changes of the electron geometries during the defluorination widen the redox window between the substrates and the products and ensure the chemoselectivity of single C(sp(3))–F bond cleavage.
format Online
Article
Text
id pubmed-10599478
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-105994782023-10-26 Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water Wang, Tao Zong, Yuan-Yuan Huang, Tao Jin, Xiao-Ling Wu, Li-Zhu Liu, Qiang Chem Sci Chemistry Visible-light-promoted site-selective and direct C–F bond functionalization of polyfluorinated iminosulfides was accomplished with alkenes and water under redox-neutral conditions, affording a diverse array of γ-lactams with a fluoro- and perfluoroalkyl-substituted carbon centre. A variety of perfluoroalkyl units, including C(2)F(5), C(3)F(7), C(4)F(9), and C(5)F(11) underwent site-selective defluorofunctionalization. This protocol allows high chemoselectivity control and shows excellent functional group tolerance. Mechanistic studies reveal that the remarkable changes of the electron geometries during the defluorination widen the redox window between the substrates and the products and ensure the chemoselectivity of single C(sp(3))–F bond cleavage. The Royal Society of Chemistry 2023-10-07 /pmc/articles/PMC10599478/ /pubmed/37886085 http://dx.doi.org/10.1039/d3sc03771a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Wang, Tao
Zong, Yuan-Yuan
Huang, Tao
Jin, Xiao-Ling
Wu, Li-Zhu
Liu, Qiang
Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water
title Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water
title_full Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water
title_fullStr Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water
title_full_unstemmed Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water
title_short Photocatalytic redox-neutral selective single C(sp(3))–F bond activation of perfluoroalkyl iminosulfides with alkenes and water
title_sort photocatalytic redox-neutral selective single c(sp(3))–f bond activation of perfluoroalkyl iminosulfides with alkenes and water
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10599478/
https://www.ncbi.nlm.nih.gov/pubmed/37886085
http://dx.doi.org/10.1039/d3sc03771a
work_keys_str_mv AT wangtao photocatalyticredoxneutralselectivesinglecsp3fbondactivationofperfluoroalkyliminosulfideswithalkenesandwater
AT zongyuanyuan photocatalyticredoxneutralselectivesinglecsp3fbondactivationofperfluoroalkyliminosulfideswithalkenesandwater
AT huangtao photocatalyticredoxneutralselectivesinglecsp3fbondactivationofperfluoroalkyliminosulfideswithalkenesandwater
AT jinxiaoling photocatalyticredoxneutralselectivesinglecsp3fbondactivationofperfluoroalkyliminosulfideswithalkenesandwater
AT wulizhu photocatalyticredoxneutralselectivesinglecsp3fbondactivationofperfluoroalkyliminosulfideswithalkenesandwater
AT liuqiang photocatalyticredoxneutralselectivesinglecsp3fbondactivationofperfluoroalkyliminosulfideswithalkenesandwater