Synthesis of Chiral Sulfoxides via Pd(II)-Catalyzed Enantioselective C-H Alkynylation/Kinetic Resolution of 2-(Arylsulfinyl)pyridines

Tao Zhou; Meng-Xue Jiang; Pu-Fan Qian; Qi-Jun Yao; Xue-Tao Xu; Kun Zhang; Bing-Feng Shi

doi:10.1021/acs.orglett.1c02918

Synthesis of Chiral Sulfoxides via Pd(II)-Catalyzed Enantioselective C-H Alkynylation/Kinetic Resolution of 2-(Arylsulfinyl)pyridines

Org Lett. 2021 Oct 15;23(20):7910-7915. doi: 10.1021/acs.orglett.1c02918. Epub 2021 Oct 4.

Authors

Tao Zhou¹, Meng-Xue Jiang², Pu-Fan Qian¹, Qi-Jun Yao¹, Xue-Tao Xu², Kun Zhang², Bing-Feng Shi^{1

3

4}

Affiliations

¹ Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
² School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China.
³ Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, China.
⁴ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China.

PMID: 34605653
DOI: 10.1021/acs.orglett.1c02918

Abstract

A Pd(II)-catalyzed enantioselective C-H alkynylation of 2-(arylsulfinyl)pyridines via kinetic resolution using cheap and commercially available l-pGlu-OH as a chiral ligand is reported. A wide range of 2-(arylsulfinyl)pyridines were compatible with this protocol, giving the alkynylation products and recovered sulfoxides in high yields with high enantioselectivities (up to 99% ee). Furthermore, the enantioenriched products can be easily transformed to several other types of chiral sulfoxide scaffolds with the retention of enantiopurity.