Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane

[Image: see text] Thiols easily react with [1.1.1]propellane to give sulfur-substituted bicyclo[1.1.1]pentanes in radical reactions, but this reactivity is not replicated in the case of heterocyclic thiols. Herein, we address this issue by electrophilically activating [1.1.1]propellane to promote it...

Descripción completa

Detalles Bibliográficos
Autores principales: Livesley, Sarah, Trueman, Bethany, Robertson, Craig M., Goundry, William R. F., Morris, James A., Aïssa, Christophe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9531248/
https://www.ncbi.nlm.nih.gov/pubmed/36130142
http://dx.doi.org/10.1021/acs.orglett.2c02875
_version_ 1784801863702413312
author Livesley, Sarah
Trueman, Bethany
Robertson, Craig M.
Goundry, William R. F.
Morris, James A.
Aïssa, Christophe
author_facet Livesley, Sarah
Trueman, Bethany
Robertson, Craig M.
Goundry, William R. F.
Morris, James A.
Aïssa, Christophe
author_sort Livesley, Sarah
collection PubMed
description [Image: see text] Thiols easily react with [1.1.1]propellane to give sulfur-substituted bicyclo[1.1.1]pentanes in radical reactions, but this reactivity is not replicated in the case of heterocyclic thiols. Herein, we address this issue by electrophilically activating [1.1.1]propellane to promote its iodo-sulfenylation with 10 classes of heterocyclic thiols in two protocols that can be conducted on a multigram scale without exclusion of air or moisture.
format Online
Article
Text
id pubmed-9531248
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-95312482022-10-05 Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane Livesley, Sarah Trueman, Bethany Robertson, Craig M. Goundry, William R. F. Morris, James A. Aïssa, Christophe Org Lett [Image: see text] Thiols easily react with [1.1.1]propellane to give sulfur-substituted bicyclo[1.1.1]pentanes in radical reactions, but this reactivity is not replicated in the case of heterocyclic thiols. Herein, we address this issue by electrophilically activating [1.1.1]propellane to promote its iodo-sulfenylation with 10 classes of heterocyclic thiols in two protocols that can be conducted on a multigram scale without exclusion of air or moisture. American Chemical Society 2022-09-21 2022-09-30 /pmc/articles/PMC9531248/ /pubmed/36130142 http://dx.doi.org/10.1021/acs.orglett.2c02875 Text en © 2022 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 Livesley, Sarah
Trueman, Bethany
Robertson, Craig M.
Goundry, William R. F.
Morris, James A.
Aïssa, Christophe
Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane
title Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane
title_full Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane
title_fullStr Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane
title_full_unstemmed Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane
title_short Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane
title_sort synthesis of sulfur-substituted bicyclo[1.1.1]pentanes by iodo-sulfenylation of [1.1.1]propellane
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9531248/
https://www.ncbi.nlm.nih.gov/pubmed/36130142
http://dx.doi.org/10.1021/acs.orglett.2c02875
work_keys_str_mv AT livesleysarah synthesisofsulfursubstitutedbicyclo111pentanesbyiodosulfenylationof111propellane
AT truemanbethany synthesisofsulfursubstitutedbicyclo111pentanesbyiodosulfenylationof111propellane
AT robertsoncraigm synthesisofsulfursubstitutedbicyclo111pentanesbyiodosulfenylationof111propellane
AT goundrywilliamrf synthesisofsulfursubstitutedbicyclo111pentanesbyiodosulfenylationof111propellane
AT morrisjamesa synthesisofsulfursubstitutedbicyclo111pentanesbyiodosulfenylationof111propellane
AT aissachristophe synthesisofsulfursubstitutedbicyclo111pentanesbyiodosulfenylationof111propellane

Ejemplares similares