Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides

A convenient Rh(III)-catalyzed C-H activation and cascade [4+2] annulation for the synthesis of naphthalenone sulfoxonium ylides has been developed. This method features perfect regioselectivity, mild and redox-neutral reaction conditions, and broad substrate tolerance with good to excellent yields....

Descripción completa

Detalles Bibliográficos
Autores principales: Song, Xiaohan, Han, Xu, Zhang, Rui, Liu, Hong, Wang, Jiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6572249/
https://www.ncbi.nlm.nih.gov/pubmed/31100874
http://dx.doi.org/10.3390/molecules24101884
_version_ 1783427596337283072
author Song, Xiaohan
Han, Xu
Zhang, Rui
Liu, Hong
Wang, Jiang
author_facet Song, Xiaohan
Han, Xu
Zhang, Rui
Liu, Hong
Wang, Jiang
author_sort Song, Xiaohan
collection PubMed
description A convenient Rh(III)-catalyzed C-H activation and cascade [4+2] annulation for the synthesis of naphthalenone sulfoxonium ylides has been developed. This method features perfect regioselectivity, mild and redox-neutral reaction conditions, and broad substrate tolerance with good to excellent yields. Preliminary mechanistic experiments were conducted and a plausible reaction mechanism was proposed. The new type naphthalenone sulfoxonium ylides could be further transformed into multi-substituted naphthols, which demonstrates the practical utility of this methodology.
format Online
Article
Text
id pubmed-6572249
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-65722492019-06-18 Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides Song, Xiaohan Han, Xu Zhang, Rui Liu, Hong Wang, Jiang Molecules Article A convenient Rh(III)-catalyzed C-H activation and cascade [4+2] annulation for the synthesis of naphthalenone sulfoxonium ylides has been developed. This method features perfect regioselectivity, mild and redox-neutral reaction conditions, and broad substrate tolerance with good to excellent yields. Preliminary mechanistic experiments were conducted and a plausible reaction mechanism was proposed. The new type naphthalenone sulfoxonium ylides could be further transformed into multi-substituted naphthols, which demonstrates the practical utility of this methodology. MDPI 2019-05-16 /pmc/articles/PMC6572249/ /pubmed/31100874 http://dx.doi.org/10.3390/molecules24101884 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Song, Xiaohan
Han, Xu
Zhang, Rui
Liu, Hong
Wang, Jiang
Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
title Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
title_full Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
title_fullStr Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
title_full_unstemmed Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
title_short Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
title_sort rhodium(iii)-catalyzed [4+2] annulation via c-h activation: synthesis of multi-substituted naphthalenone sulfoxonium ylides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6572249/
https://www.ncbi.nlm.nih.gov/pubmed/31100874
http://dx.doi.org/10.3390/molecules24101884
work_keys_str_mv AT songxiaohan rhodiumiiicatalyzed42annulationviachactivationsynthesisofmultisubstitutednaphthalenonesulfoxoniumylides
AT hanxu rhodiumiiicatalyzed42annulationviachactivationsynthesisofmultisubstitutednaphthalenonesulfoxoniumylides
AT zhangrui rhodiumiiicatalyzed42annulationviachactivationsynthesisofmultisubstitutednaphthalenonesulfoxoniumylides
AT liuhong rhodiumiiicatalyzed42annulationviachactivationsynthesisofmultisubstitutednaphthalenonesulfoxoniumylides
AT wangjiang rhodiumiiicatalyzed42annulationviachactivationsynthesisofmultisubstitutednaphthalenonesulfoxoniumylides

Ejemplares similares