Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst

Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization–endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine...

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Detalles Bibliográficos
Autores principales: Gesmundo, Nathan J, Nicewicz, David A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077508/
https://www.ncbi.nlm.nih.gov/pubmed/24991279
http://dx.doi.org/10.3762/bjoc.10.128
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author Gesmundo, Nathan J
Nicewicz, David A
author_facet Gesmundo, Nathan J
Nicewicz, David A
author_sort Gesmundo, Nathan J
collection PubMed
description Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization–endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine the structural requirements necessary for successful reactivity. Several unique endoperoxide structures were synthesized in yields up to 79%.
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spelling pubmed-40775082014-07-02 Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst Gesmundo, Nathan J Nicewicz, David A Beilstein J Org Chem Letter Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization–endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine the structural requirements necessary for successful reactivity. Several unique endoperoxide structures were synthesized in yields up to 79%. Beilstein-Institut 2014-06-03 /pmc/articles/PMC4077508/ /pubmed/24991279 http://dx.doi.org/10.3762/bjoc.10.128 Text en Copyright © 2014, Gesmundo and Nicewicz https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Gesmundo, Nathan J
Nicewicz, David A
Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
title Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
title_full Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
title_fullStr Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
title_full_unstemmed Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
title_short Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
title_sort cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077508/
https://www.ncbi.nlm.nih.gov/pubmed/24991279
http://dx.doi.org/10.3762/bjoc.10.128
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