Cargando…

One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones

Reported here is the direct synthesis of naphthofurans and benzofurans from readily available phenols and α-haloketones promoted by titanium tetrachloride which combines Friedel–Crafts-like alkylation and intramolecular cyclodehydration into one step. This simple protocol allows for the formation of...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Bingqiao, Zhang, Qiu, Luo, Juan, Gan, Zongjie, Jiang, Wengao, Tang, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600630/
https://www.ncbi.nlm.nih.gov/pubmed/31212606
http://dx.doi.org/10.3390/molecules24112187
_version_ 1783431153263312896
author Wang, Bingqiao
Zhang, Qiu
Luo, Juan
Gan, Zongjie
Jiang, Wengao
Tang, Qiang
author_facet Wang, Bingqiao
Zhang, Qiu
Luo, Juan
Gan, Zongjie
Jiang, Wengao
Tang, Qiang
author_sort Wang, Bingqiao
collection PubMed
description Reported here is the direct synthesis of naphthofurans and benzofurans from readily available phenols and α-haloketones promoted by titanium tetrachloride which combines Friedel–Crafts-like alkylation and intramolecular cyclodehydration into one step. This simple protocol allows for the formation of a variety of high value naphthofurans and benzofurans within which a series of cyclic and acyclic groups are readily incorporated. This process demonstrates the advantages of high levels of regioselectivity, broad substrate scope, and moderate to excellent yields.
format Online
Article
Text
id pubmed-6600630
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-66006302019-07-16 One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones Wang, Bingqiao Zhang, Qiu Luo, Juan Gan, Zongjie Jiang, Wengao Tang, Qiang Molecules Article Reported here is the direct synthesis of naphthofurans and benzofurans from readily available phenols and α-haloketones promoted by titanium tetrachloride which combines Friedel–Crafts-like alkylation and intramolecular cyclodehydration into one step. This simple protocol allows for the formation of a variety of high value naphthofurans and benzofurans within which a series of cyclic and acyclic groups are readily incorporated. This process demonstrates the advantages of high levels of regioselectivity, broad substrate scope, and moderate to excellent yields. MDPI 2019-06-11 /pmc/articles/PMC6600630/ /pubmed/31212606 http://dx.doi.org/10.3390/molecules24112187 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Bingqiao
Zhang, Qiu
Luo, Juan
Gan, Zongjie
Jiang, Wengao
Tang, Qiang
One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones
title One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones
title_full One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones
title_fullStr One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones
title_full_unstemmed One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones
title_short One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones
title_sort one-step regioselective synthesis of benzofurans from phenols and α-haloketones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600630/
https://www.ncbi.nlm.nih.gov/pubmed/31212606
http://dx.doi.org/10.3390/molecules24112187
work_keys_str_mv AT wangbingqiao onestepregioselectivesynthesisofbenzofuransfromphenolsandahaloketones
AT zhangqiu onestepregioselectivesynthesisofbenzofuransfromphenolsandahaloketones
AT luojuan onestepregioselectivesynthesisofbenzofuransfromphenolsandahaloketones
AT ganzongjie onestepregioselectivesynthesisofbenzofuransfromphenolsandahaloketones
AT jiangwengao onestepregioselectivesynthesisofbenzofuransfromphenolsandahaloketones
AT tangqiang onestepregioselectivesynthesisofbenzofuransfromphenolsandahaloketones