Cargando…

Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds

A new process has been developed for the palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C–H and C–S bonds. In contrast to the existing methods for the synthesis of this scaffold by C–H functionalization, this new catalytic C–H/C–S coupling method does not requi...

Descripción completa

Detalles Bibliográficos
Autores principales: Tobisu, Mamoru, Masuya, Yoshihiro, Baba, Katsuaki, Chatani, Naoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5477049/
https://www.ncbi.nlm.nih.gov/pubmed/28660030
http://dx.doi.org/10.1039/c5sc04890g
_version_ 1783244713232433152
author Tobisu, Mamoru
Masuya, Yoshihiro
Baba, Katsuaki
Chatani, Naoto
author_facet Tobisu, Mamoru
Masuya, Yoshihiro
Baba, Katsuaki
Chatani, Naoto
author_sort Tobisu, Mamoru
collection PubMed
description A new process has been developed for the palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C–H and C–S bonds. In contrast to the existing methods for the synthesis of this scaffold by C–H functionalization, this new catalytic C–H/C–S coupling method does not require the presence of an external stoichiometric oxidant or reactive functionalities such as C–X or S–H, allowing its application to the synthesis of elaborate π-systems. Notably, the product-forming step of this reaction lies in an oxidative addition step rather than a reductive elimination step, making this reaction mechanistically uncommon.
format Online
Article
Text
id pubmed-5477049
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-54770492017-06-28 Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds Tobisu, Mamoru Masuya, Yoshihiro Baba, Katsuaki Chatani, Naoto Chem Sci Chemistry A new process has been developed for the palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C–H and C–S bonds. In contrast to the existing methods for the synthesis of this scaffold by C–H functionalization, this new catalytic C–H/C–S coupling method does not require the presence of an external stoichiometric oxidant or reactive functionalities such as C–X or S–H, allowing its application to the synthesis of elaborate π-systems. Notably, the product-forming step of this reaction lies in an oxidative addition step rather than a reductive elimination step, making this reaction mechanistically uncommon. Royal Society of Chemistry 2016-04-01 2016-01-21 /pmc/articles/PMC5477049/ /pubmed/28660030 http://dx.doi.org/10.1039/c5sc04890g Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Tobisu, Mamoru
Masuya, Yoshihiro
Baba, Katsuaki
Chatani, Naoto
Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
title Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
title_full Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
title_fullStr Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
title_full_unstemmed Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
title_short Palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
title_sort palladium(ii)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5477049/
https://www.ncbi.nlm.nih.gov/pubmed/28660030
http://dx.doi.org/10.1039/c5sc04890g
work_keys_str_mv AT tobisumamoru palladiumiicatalyzedsynthesisofdibenzothiophenederivativesviathecleavageofcarbonsulfurandcarbonhydrogenbonds
AT masuyayoshihiro palladiumiicatalyzedsynthesisofdibenzothiophenederivativesviathecleavageofcarbonsulfurandcarbonhydrogenbonds
AT babakatsuaki palladiumiicatalyzedsynthesisofdibenzothiophenederivativesviathecleavageofcarbonsulfurandcarbonhydrogenbonds
AT chataninaoto palladiumiicatalyzedsynthesisofdibenzothiophenederivativesviathecleavageofcarbonsulfurandcarbonhydrogenbonds