Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation

A metal- and aldehyde-free visible-light-driven photoredox-neutral alkene acylarylation with readily available cyanoarenes is described. A variety of 3-(arylmethyl)chroman-4-ones (i.e., homoisoflavonoids) and analogs are efficiently synthesized with good functional group tolerance. This mild protoco...

Descripción completa

Detalles Bibliográficos
Autores principales: Ding, Yan, Yu, Shengjiao, Ren, Man, Lu, Ji, Fu, Qiang, Zhang, Zhijie, Wang, Qin, Bai, Jun, Hao, Na, Yang, Lin, Wei, Siping, Yi, Dong, Wei, Jun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9660241/
https://www.ncbi.nlm.nih.gov/pubmed/36385990
http://dx.doi.org/10.3389/fchem.2022.1059792
_version_ 1784830378806083584
author Ding, Yan
Yu, Shengjiao
Ren, Man
Lu, Ji
Fu, Qiang
Zhang, Zhijie
Wang, Qin
Bai, Jun
Hao, Na
Yang, Lin
Wei, Siping
Yi, Dong
Wei, Jun
author_facet Ding, Yan
Yu, Shengjiao
Ren, Man
Lu, Ji
Fu, Qiang
Zhang, Zhijie
Wang, Qin
Bai, Jun
Hao, Na
Yang, Lin
Wei, Siping
Yi, Dong
Wei, Jun
author_sort Ding, Yan
collection PubMed
description A metal- and aldehyde-free visible-light-driven photoredox-neutral alkene acylarylation with readily available cyanoarenes is described. A variety of 3-(arylmethyl)chroman-4-ones (i.e., homoisoflavonoids) and analogs are efficiently synthesized with good functional group tolerance. This mild protocol relies on a phosphoranyl radical-mediated acyl radical-initiated cyclization and selective radical-radical coupling sequence, and is also further highlighted by subsequent derivatization to chromone and 2H-chromene as well as its application in the three-component alkene acylarylation.
format Online
Article
Text
id pubmed-9660241
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher Frontiers Media S.A.
record_format MEDLINE/PubMed
spelling pubmed-96602412022-11-15 Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation Ding, Yan Yu, Shengjiao Ren, Man Lu, Ji Fu, Qiang Zhang, Zhijie Wang, Qin Bai, Jun Hao, Na Yang, Lin Wei, Siping Yi, Dong Wei, Jun Front Chem Chemistry A metal- and aldehyde-free visible-light-driven photoredox-neutral alkene acylarylation with readily available cyanoarenes is described. A variety of 3-(arylmethyl)chroman-4-ones (i.e., homoisoflavonoids) and analogs are efficiently synthesized with good functional group tolerance. This mild protocol relies on a phosphoranyl radical-mediated acyl radical-initiated cyclization and selective radical-radical coupling sequence, and is also further highlighted by subsequent derivatization to chromone and 2H-chromene as well as its application in the three-component alkene acylarylation. Frontiers Media S.A. 2022-10-31 /pmc/articles/PMC9660241/ /pubmed/36385990 http://dx.doi.org/10.3389/fchem.2022.1059792 Text en Copyright © 2022 Ding, Yu, Ren, Lu, Fu, Zhang, Wang, Bai, Hao, Yang, Wei, Yi and Wei. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Ding, Yan
Yu, Shengjiao
Ren, Man
Lu, Ji
Fu, Qiang
Zhang, Zhijie
Wang, Qin
Bai, Jun
Hao, Na
Yang, Lin
Wei, Siping
Yi, Dong
Wei, Jun
Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation
title Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation
title_full Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation
title_fullStr Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation
title_full_unstemmed Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation
title_short Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation
title_sort redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9660241/
https://www.ncbi.nlm.nih.gov/pubmed/36385990
http://dx.doi.org/10.3389/fchem.2022.1059792
work_keys_str_mv AT dingyan redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT yushengjiao redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT renman redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT luji redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT fuqiang redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT zhangzhijie redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT wangqin redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT baijun redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT haona redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT yanglin redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT weisiping redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT yidong redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation
AT weijun redoxneutralandmetalfreesynthesisof3arylmethylchroman4onesviavisiblelightdrivenalkeneacylarylation

Ejemplares similares