Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence

[Image: see text] Arylsulfinyl groups direct the metal-free, regiospecific, nucleophilic ortho-allylation of pyrroles and pyrazoles. Mechanistic studies support the intermediacy of allylsulfonium salts that undergo facile thio-Claisen rearrangement onto the heterocyclic ring, giving products of coup...

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Autores principales: Eberhart, Andrew J., Cicoira, Claudio, Procter, David J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2013
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3819180/
https://www.ncbi.nlm.nih.gov/pubmed/23855635
http://dx.doi.org/10.1021/ol401786d
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author Eberhart, Andrew J.
Cicoira, Claudio
Procter, David J.
author_facet Eberhart, Andrew J.
Cicoira, Claudio
Procter, David J.
author_sort Eberhart, Andrew J.
collection PubMed
description [Image: see text] Arylsulfinyl groups direct the metal-free, regiospecific, nucleophilic ortho-allylation of pyrroles and pyrazoles. Mechanistic studies support the intermediacy of allylsulfonium salts that undergo facile thio-Claisen rearrangement onto the heterocyclic ring, giving products of coupling. The strategy has been adapted to allow regiospecific propargylation of the heterocyclic substrates.
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spelling pubmed-38191802013-11-06 Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence Eberhart, Andrew J. Cicoira, Claudio Procter, David J. Org Lett [Image: see text] Arylsulfinyl groups direct the metal-free, regiospecific, nucleophilic ortho-allylation of pyrroles and pyrazoles. Mechanistic studies support the intermediacy of allylsulfonium salts that undergo facile thio-Claisen rearrangement onto the heterocyclic ring, giving products of coupling. The strategy has been adapted to allow regiospecific propargylation of the heterocyclic substrates. American Chemical Society 2013-07-15 2013-08-02 /pmc/articles/PMC3819180/ /pubmed/23855635 http://dx.doi.org/10.1021/ol401786d Text en Copyright © 2013 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Eberhart, Andrew J.
Cicoira, Claudio
Procter, David J.
Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
title Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
title_full Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
title_fullStr Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
title_full_unstemmed Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
title_short Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
title_sort nucleophilic ortho-allylation of pyrroles and pyrazoles: an accelerated pummerer/thio-claisen rearrangement sequence
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3819180/
https://www.ncbi.nlm.nih.gov/pubmed/23855635
http://dx.doi.org/10.1021/ol401786d
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