Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes

Visible light induced singlet nucleophilic carbenes undergo rapid [2 + 1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation process requires only visible light irradiation to proceed, circumventing the use of exogenou...

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Autores principales: Bunyamin, Amanda, Hua, Carol, Polyzos, Anastasios, Priebbenow, Daniel L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8926286/
https://www.ncbi.nlm.nih.gov/pubmed/35414869
http://dx.doi.org/10.1039/d2sc00203e
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author Bunyamin, Amanda
Hua, Carol
Polyzos, Anastasios
Priebbenow, Daniel L.
author_facet Bunyamin, Amanda
Hua, Carol
Polyzos, Anastasios
Priebbenow, Daniel L.
author_sort Bunyamin, Amanda
collection PubMed
description Visible light induced singlet nucleophilic carbenes undergo rapid [2 + 1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation process requires only visible light irradiation to proceed, circumventing the use of exogenous (photo)catalysts, sensitisers or additives and showcases a vastly underexplored mode of reactivity for nucleophilic carbenes in chemical synthesis. The discovery of additional transformations including a cyclopropanation/retro-Michael/Michael cascade process to afford chromanones and a photochemical C–H insertion reaction are also described.
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spelling pubmed-89262862022-04-11 Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes Bunyamin, Amanda Hua, Carol Polyzos, Anastasios Priebbenow, Daniel L. Chem Sci Chemistry Visible light induced singlet nucleophilic carbenes undergo rapid [2 + 1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation process requires only visible light irradiation to proceed, circumventing the use of exogenous (photo)catalysts, sensitisers or additives and showcases a vastly underexplored mode of reactivity for nucleophilic carbenes in chemical synthesis. The discovery of additional transformations including a cyclopropanation/retro-Michael/Michael cascade process to afford chromanones and a photochemical C–H insertion reaction are also described. The Royal Society of Chemistry 2022-02-25 /pmc/articles/PMC8926286/ /pubmed/35414869 http://dx.doi.org/10.1039/d2sc00203e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Bunyamin, Amanda
Hua, Carol
Polyzos, Anastasios
Priebbenow, Daniel L.
Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
title Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
title_full Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
title_fullStr Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
title_full_unstemmed Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
title_short Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
title_sort intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8926286/
https://www.ncbi.nlm.nih.gov/pubmed/35414869
http://dx.doi.org/10.1039/d2sc00203e
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AT huacarol intramolecularphotochemical21cycloadditionsofnucleophilicsiloxycarbenes
AT polyzosanastasios intramolecularphotochemical21cycloadditionsofnucleophilicsiloxycarbenes
AT priebbenowdaniell intramolecularphotochemical21cycloadditionsofnucleophilicsiloxycarbenes

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