Issue 18, 2024
From the journal:

Chemical Science

Palladium-catalyzed regio- and stereo-selective phosphination of cyclic biarylsulfonium salts to access atropoisomeric phosphines†

Jinghui Sun,‡a   Yifei Yan,‡a   Xuanxuan Chen,a   Zhiwei Huanga  and  Yinhua Huang ORCID logo *a  

* Corresponding authors

a College of Materials, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, P. R. China
E-mail: yhhuang@hznu.edu.cn

Abstract

A palladium-catalyzed regio- and stereo-selective phosphination of cyclic biarylsulfonium salts (racemic) with HPAr3Ar4 for straightforward synthesis of atropoisomeric phosphines (P,S-ligands) bearing a stereogenic axis or both a stereogenic axis and a P-stereogenic center is reported. The high reactivity and regio- and stereo-selectivity originate from the torsional strain release and palladium catalysis, and the construction of a P-stereogenic center is enabled by an efficient dynamic kinetic resolution. The high performance of the nascent P,S-ligands has been demonstrated in palladium-catalyzed asymmetric allylic substitutions, indicating the great potential of the present methodology.

Graphical abstract: Palladium-catalyzed regio- and stereo-selective phosphination of cyclic biarylsulfonium salts to access atropoisomeric phosphines

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Article information

DOI
https://doi.org/10.1039/D4SC00446A
Article type
Edge Article
Submitted
19 Jan 2024
Accepted
08 Apr 2024
First published
09 Apr 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 6943-6948

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Palladium-catalyzed regio- and stereo-selective phosphination of cyclic biarylsulfonium salts to access atropoisomeric phosphines

J. Sun, Y. Yan, X. Chen, Z. Huang and Y. Huang, Chem. Sci., 2024, 15, 6943 DOI: 10.1039/D4SC00446A

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