Electrophilic Trapping of Semibenzenes

[Image: see text] In this work, we demonstrate how allylative dearomatization of benzyl chlorides can provide direct access to a variety of semibenzenes. These scaffolds behave as highly reactive nucleophiles in the presence of carbocations. In addition, semibenzenes are susceptible to intramolecula...

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Autores principales: Boldrini, Cosimo, Reis, Marta Castiñeira, Harutyunyan, Syuzanna R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552181/
https://www.ncbi.nlm.nih.gov/pubmed/36095222
http://dx.doi.org/10.1021/acs.joc.2c01331
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author Boldrini, Cosimo
Reis, Marta Castiñeira
Harutyunyan, Syuzanna R.
author_facet Boldrini, Cosimo
Reis, Marta Castiñeira
Harutyunyan, Syuzanna R.
author_sort Boldrini, Cosimo
collection PubMed
description [Image: see text] In this work, we demonstrate how allylative dearomatization of benzyl chlorides can provide direct access to a variety of semibenzenes. These scaffolds behave as highly reactive nucleophiles in the presence of carbocations. In addition, semibenzenes are susceptible to intramolecular rearrangements rendering a broad scope of functionalized arenes. An analysis of this new reactivity is reported, as well as the rationale behind the observed intramolecular reorganizations.
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spelling pubmed-95521812022-10-12 Electrophilic Trapping of Semibenzenes Boldrini, Cosimo Reis, Marta Castiñeira Harutyunyan, Syuzanna R. J Org Chem [Image: see text] In this work, we demonstrate how allylative dearomatization of benzyl chlorides can provide direct access to a variety of semibenzenes. These scaffolds behave as highly reactive nucleophiles in the presence of carbocations. In addition, semibenzenes are susceptible to intramolecular rearrangements rendering a broad scope of functionalized arenes. An analysis of this new reactivity is reported, as well as the rationale behind the observed intramolecular reorganizations. American Chemical Society 2022-09-12 2022-10-07 /pmc/articles/PMC9552181/ /pubmed/36095222 http://dx.doi.org/10.1021/acs.joc.2c01331 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Boldrini, Cosimo
Reis, Marta Castiñeira
Harutyunyan, Syuzanna R.
Electrophilic Trapping of Semibenzenes
title Electrophilic Trapping of Semibenzenes
title_full Electrophilic Trapping of Semibenzenes
title_fullStr Electrophilic Trapping of Semibenzenes
title_full_unstemmed Electrophilic Trapping of Semibenzenes
title_short Electrophilic Trapping of Semibenzenes
title_sort electrophilic trapping of semibenzenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552181/
https://www.ncbi.nlm.nih.gov/pubmed/36095222
http://dx.doi.org/10.1021/acs.joc.2c01331
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AT harutyunyansyuzannar electrophilictrappingofsemibenzenes

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