Reductive radical-initiated 1,2-C migration assisted by an azidyl group

We report here a novel reductive radical-polar crossover reaction that is a reductive radical-initiated 1,2-C migration of 2-azido allyl alcohols enabled by an azidyl group. The reaction tolerates diverse migrating groups, such as alkyl, alkenyl, and aryl groups, allowing access to n+1 ring expansio...

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Detalles Bibliográficos
Autores principales: Zhang, Xueying, Zhang, Zhansong, Song, Jin-Na, Wang, Zikun
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/PMC8163324/
https://www.ncbi.nlm.nih.gov/pubmed/34123076
http://dx.doi.org/10.1039/d0sc02559c
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author Zhang, Xueying
Zhang, Zhansong
Song, Jin-Na
Wang, Zikun
author_facet Zhang, Xueying
Zhang, Zhansong
Song, Jin-Na
Wang, Zikun
author_sort Zhang, Xueying
collection PubMed
description We report here a novel reductive radical-polar crossover reaction that is a reductive radical-initiated 1,2-C migration of 2-azido allyl alcohols enabled by an azidyl group. The reaction tolerates diverse migrating groups, such as alkyl, alkenyl, and aryl groups, allowing access to n+1 ring expansion of small to large rings. The possibility of directly using propargyl alcohols in one-pot is also described. Mechanistic studies indicated that an azidyl group is a good leaving group and provides a driving force for the 1,2-C migration.
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spelling pubmed-81633242021-06-11 Reductive radical-initiated 1,2-C migration assisted by an azidyl group Zhang, Xueying Zhang, Zhansong Song, Jin-Na Wang, Zikun Chem Sci Chemistry We report here a novel reductive radical-polar crossover reaction that is a reductive radical-initiated 1,2-C migration of 2-azido allyl alcohols enabled by an azidyl group. The reaction tolerates diverse migrating groups, such as alkyl, alkenyl, and aryl groups, allowing access to n+1 ring expansion of small to large rings. The possibility of directly using propargyl alcohols in one-pot is also described. Mechanistic studies indicated that an azidyl group is a good leaving group and provides a driving force for the 1,2-C migration. The Royal Society of Chemistry 2020-07-07 /pmc/articles/PMC8163324/ /pubmed/34123076 http://dx.doi.org/10.1039/d0sc02559c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Zhang, Xueying
Zhang, Zhansong
Song, Jin-Na
Wang, Zikun
Reductive radical-initiated 1,2-C migration assisted by an azidyl group
title Reductive radical-initiated 1,2-C migration assisted by an azidyl group
title_full Reductive radical-initiated 1,2-C migration assisted by an azidyl group
title_fullStr Reductive radical-initiated 1,2-C migration assisted by an azidyl group
title_full_unstemmed Reductive radical-initiated 1,2-C migration assisted by an azidyl group
title_short Reductive radical-initiated 1,2-C migration assisted by an azidyl group
title_sort reductive radical-initiated 1,2-c migration assisted by an azidyl group
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163324/
https://www.ncbi.nlm.nih.gov/pubmed/34123076
http://dx.doi.org/10.1039/d0sc02559c
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AT zhangzhansong reductiveradicalinitiated12cmigrationassistedbyanazidylgroup
AT songjinna reductiveradicalinitiated12cmigrationassistedbyanazidylgroup
AT wangzikun reductiveradicalinitiated12cmigrationassistedbyanazidylgroup

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