Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes

[Image: see text] Herein we report an example of tandem oxidative acetoxylation/carbocyclization of arylallenes 1 using Pd(OAc)(2). The catalytic protocol is highly selective and provides access to new C–C and C–O bonds leading to a carbocyclization. The reaction proceeds via C–H activation by Pd. M...

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Autores principales: Mazuela, Javier, Banerjee, Debasis, Bäckvall, Jan-E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4557776/
https://www.ncbi.nlm.nih.gov/pubmed/26201012
http://dx.doi.org/10.1021/jacs.5b06068
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author Mazuela, Javier
Banerjee, Debasis
Bäckvall, Jan-E.
author_facet Mazuela, Javier
Banerjee, Debasis
Bäckvall, Jan-E.
author_sort Mazuela, Javier
collection PubMed
description [Image: see text] Herein we report an example of tandem oxidative acetoxylation/carbocyclization of arylallenes 1 using Pd(OAc)(2). The catalytic protocol is highly selective and provides access to new C–C and C–O bonds leading to a carbocyclization. The reaction proceeds via C–H activation by Pd. Mechanistic investigations show that the C–H activation is not the rate-limiting step and indicate that the reaction proceeds via acetoxylation of the allene.
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spelling pubmed-45577762015-09-08 Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes Mazuela, Javier Banerjee, Debasis Bäckvall, Jan-E. J Am Chem Soc [Image: see text] Herein we report an example of tandem oxidative acetoxylation/carbocyclization of arylallenes 1 using Pd(OAc)(2). The catalytic protocol is highly selective and provides access to new C–C and C–O bonds leading to a carbocyclization. The reaction proceeds via C–H activation by Pd. Mechanistic investigations show that the C–H activation is not the rate-limiting step and indicate that the reaction proceeds via acetoxylation of the allene. American Chemical Society 2015-07-22 2015-08-05 /pmc/articles/PMC4557776/ /pubmed/26201012 http://dx.doi.org/10.1021/jacs.5b06068 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 Mazuela, Javier
Banerjee, Debasis
Bäckvall, Jan-E.
Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes
title Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes
title_full Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes
title_fullStr Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes
title_full_unstemmed Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes
title_short Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes
title_sort palladium(ii)-catalyzed tandem oxidative acetoxylation/ortho c–h activation/carbocyclization of arylallenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4557776/
https://www.ncbi.nlm.nih.gov/pubmed/26201012
http://dx.doi.org/10.1021/jacs.5b06068
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AT banerjeedebasis palladiumiicatalyzedtandemoxidativeacetoxylationorthochactivationcarbocyclizationofarylallenes
AT backvalljane palladiumiicatalyzedtandemoxidativeacetoxylationorthochactivationcarbocyclizationofarylallenes

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