Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium

A palladium-catalyzed enantioselective ring-opening/carbonylation of cyclic diarylsulfonium salts is reported. In comparison to thioethers, the sulfonium salts displayed high reactivity and enabled the reaction to be performed under mild conditions (room temperature). The steric repulsion of the two...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Qiuchi, Xue, Xiaoping, Hong, Biqiong, Gu, Zhenhua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8966737/
https://www.ncbi.nlm.nih.gov/pubmed/35432889
http://dx.doi.org/10.1039/d2sc00341d
_version_ 1784678706580553728
author Zhang, Qiuchi
Xue, Xiaoping
Hong, Biqiong
Gu, Zhenhua
author_facet Zhang, Qiuchi
Xue, Xiaoping
Hong, Biqiong
Gu, Zhenhua
author_sort Zhang, Qiuchi
collection PubMed
description A palladium-catalyzed enantioselective ring-opening/carbonylation of cyclic diarylsulfonium salts is reported. In comparison to thioethers, the sulfonium salts displayed high reactivity and enabled the reaction to be performed under mild conditions (room temperature). The steric repulsion of the two non-hydrogen substituents adjacent to the axis led cyclic diarylsulfonium salts to be distorted, which enabled the ring-opening reaction to proceed with significant preference for breaking the exocyclic C–S bond.
format Online
Article
Text
id pubmed-8966737
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-89667372022-04-14 Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium Zhang, Qiuchi Xue, Xiaoping Hong, Biqiong Gu, Zhenhua Chem Sci Chemistry A palladium-catalyzed enantioselective ring-opening/carbonylation of cyclic diarylsulfonium salts is reported. In comparison to thioethers, the sulfonium salts displayed high reactivity and enabled the reaction to be performed under mild conditions (room temperature). The steric repulsion of the two non-hydrogen substituents adjacent to the axis led cyclic diarylsulfonium salts to be distorted, which enabled the ring-opening reaction to proceed with significant preference for breaking the exocyclic C–S bond. The Royal Society of Chemistry 2022-03-01 /pmc/articles/PMC8966737/ /pubmed/35432889 http://dx.doi.org/10.1039/d2sc00341d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Zhang, Qiuchi
Xue, Xiaoping
Hong, Biqiong
Gu, Zhenhua
Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium
title Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium
title_full Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium
title_fullStr Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium
title_full_unstemmed Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium
title_short Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium
title_sort torsional strain inversed chemoselectivity in a pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8966737/
https://www.ncbi.nlm.nih.gov/pubmed/35432889
http://dx.doi.org/10.1039/d2sc00341d
work_keys_str_mv AT zhangqiuchi torsionalstraininversedchemoselectivityinapdcatalyzedatroposelectivecarbonylationreactionofdibenzothiophenium
AT xuexiaoping torsionalstraininversedchemoselectivityinapdcatalyzedatroposelectivecarbonylationreactionofdibenzothiophenium
AT hongbiqiong torsionalstraininversedchemoselectivityinapdcatalyzedatroposelectivecarbonylationreactionofdibenzothiophenium
AT guzhenhua torsionalstraininversedchemoselectivityinapdcatalyzedatroposelectivecarbonylationreactionofdibenzothiophenium

Ejemplares similares