A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones

A facile, efficient and metal free one-flask approach to diversely substituted furans from easily accessible 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones is reported. This protocol integrates three steps of cyclopropanation, Cloke–Wilson rearrangement and elimination of HCl in one-flask to gi...

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Detalles Bibliográficos
Autores principales: Zhang, Zixin, Huang, Aimin, Ma, Lin, Xu, Jian-hua, Zhang, Min
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/PMC9115646/
https://www.ncbi.nlm.nih.gov/pubmed/35702439
http://dx.doi.org/10.1039/d2ra01472f
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author Zhang, Zixin
Huang, Aimin
Ma, Lin
Xu, Jian-hua
Zhang, Min
author_facet Zhang, Zixin
Huang, Aimin
Ma, Lin
Xu, Jian-hua
Zhang, Min
author_sort Zhang, Zixin
collection PubMed
description A facile, efficient and metal free one-flask approach to diversely substituted furans from easily accessible 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones is reported. This protocol integrates three steps of cyclopropanation, Cloke–Wilson rearrangement and elimination of HCl in one-flask to give products in moderate to good yields. It provides a metal and oxidant free approach to multi-substituted furans with the advantages of easy operation, mild reaction conditions and a broad scope of substrates.
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spelling pubmed-91156462022-06-13 A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones Zhang, Zixin Huang, Aimin Ma, Lin Xu, Jian-hua Zhang, Min RSC Adv Chemistry A facile, efficient and metal free one-flask approach to diversely substituted furans from easily accessible 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones is reported. This protocol integrates three steps of cyclopropanation, Cloke–Wilson rearrangement and elimination of HCl in one-flask to give products in moderate to good yields. It provides a metal and oxidant free approach to multi-substituted furans with the advantages of easy operation, mild reaction conditions and a broad scope of substrates. The Royal Society of Chemistry 2022-05-18 /pmc/articles/PMC9115646/ /pubmed/35702439 http://dx.doi.org/10.1039/d2ra01472f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Zhang, Zixin
Huang, Aimin
Ma, Lin
Xu, Jian-hua
Zhang, Min
A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
title A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
title_full A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
title_fullStr A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
title_full_unstemmed A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
title_short A facile metal-free one-flask synthesis of multi-substituted furans via a BF(3)·Et(2)O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
title_sort facile metal-free one-flask synthesis of multi-substituted furans via a bf(3)·et(2)o mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9115646/
https://www.ncbi.nlm.nih.gov/pubmed/35702439
http://dx.doi.org/10.1039/d2ra01472f
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