Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

[Image: see text] A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion–oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts....

Descripción completa

Detalles Bibliográficos
Autores principales: Shu, Xing-zhong, Zhang, Miao, He, Ying, Frei, Heinz, Toste, F. Dean
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4333587/
https://www.ncbi.nlm.nih.gov/pubmed/24730447
http://dx.doi.org/10.1021/ja500716j
_version_ 1782358066505711616
author Shu, Xing-zhong
Zhang, Miao
He, Ying
Frei, Heinz
Toste, F. Dean
author_facet Shu, Xing-zhong
Zhang, Miao
He, Ying
Frei, Heinz
Toste, F. Dean
author_sort Shu, Xing-zhong
collection PubMed
description [Image: see text] A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion–oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)–aryl intermediate is proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy.
format Online
Article
Text
id pubmed-4333587
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-43335872015-04-14 Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion Shu, Xing-zhong Zhang, Miao He, Ying Frei, Heinz Toste, F. Dean J Am Chem Soc [Image: see text] A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion–oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)–aryl intermediate is proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy. American Chemical Society 2014-04-14 2014-04-23 /pmc/articles/PMC4333587/ /pubmed/24730447 http://dx.doi.org/10.1021/ja500716j Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Shu, Xing-zhong
Zhang, Miao
He, Ying
Frei, Heinz
Toste, F. Dean
Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion
title Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion
title_full Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion
title_fullStr Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion
title_full_unstemmed Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion
title_short Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion
title_sort dual visible light photoredox and gold-catalyzed arylative ring expansion
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4333587/
https://www.ncbi.nlm.nih.gov/pubmed/24730447
http://dx.doi.org/10.1021/ja500716j
work_keys_str_mv AT shuxingzhong dualvisiblelightphotoredoxandgoldcatalyzedarylativeringexpansion
AT zhangmiao dualvisiblelightphotoredoxandgoldcatalyzedarylativeringexpansion
AT heying dualvisiblelightphotoredoxandgoldcatalyzedarylativeringexpansion
AT freiheinz dualvisiblelightphotoredoxandgoldcatalyzedarylativeringexpansion
AT tostefdean dualvisiblelightphotoredoxandgoldcatalyzedarylativeringexpansion

Ejemplares similares