Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles

[Image: see text] The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho–ortho′ coupling pattern were obtained with high selectivity. Further oxidation led to ortho′–ortho′ coupling to generat...

Descripción completa

Detalles Bibliográficos
Autores principales: Liu, Lei, Carroll, Patrick J., Kozlowski, Marisa C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4576935/
https://www.ncbi.nlm.nih.gov/pubmed/25590578
http://dx.doi.org/10.1021/ol503521b
_version_ 1782390923482628096
author Liu, Lei
Carroll, Patrick J.
Kozlowski, Marisa C.
author_facet Liu, Lei
Carroll, Patrick J.
Kozlowski, Marisa C.
author_sort Liu, Lei
collection PubMed
description [Image: see text] The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho–ortho′ coupling pattern were obtained with high selectivity. Further oxidation led to ortho′–ortho′ coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.
format Online
Article
Text
id pubmed-4576935
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-45769352016-01-15 Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles Liu, Lei Carroll, Patrick J. Kozlowski, Marisa C. Org Lett [Image: see text] The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho–ortho′ coupling pattern were obtained with high selectivity. Further oxidation led to ortho′–ortho′ coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected. American Chemical Society 2015-01-15 2015-02-06 /pmc/articles/PMC4576935/ /pubmed/25590578 http://dx.doi.org/10.1021/ol503521b Text en Copyright © 2015 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 Liu, Lei
Carroll, Patrick J.
Kozlowski, Marisa C.
Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
title Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
title_full Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
title_fullStr Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
title_full_unstemmed Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
title_short Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
title_sort vanadium-catalyzed regioselective oxidative coupling of 2-hydroxycarbazoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4576935/
https://www.ncbi.nlm.nih.gov/pubmed/25590578
http://dx.doi.org/10.1021/ol503521b
work_keys_str_mv AT liulei vanadiumcatalyzedregioselectiveoxidativecouplingof2hydroxycarbazoles
AT carrollpatrickj vanadiumcatalyzedregioselectiveoxidativecouplingof2hydroxycarbazoles
AT kozlowskimarisac vanadiumcatalyzedregioselectiveoxidativecouplingof2hydroxycarbazoles

Ejemplares similares