Catalytic Enantioselective Reductive Arylation and Alkenylation of Sulfinylamines to Access Sulfinamides Enabled by Cobalt Catalysis

Y Yin Yuan X Xinyu Tian (State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry) H Hongxia Zheng (Department of Chemistry Fudan University 2205 Songhu Road Shanghai 200438 China) Y Yuze Li (Heilongjiang Provincial Hospital) J Junliang Zhang (Institute of Fuel Cells, School of Mechanical Engineering, MOE Key Laboratory of Power & Machinery Engineering) J Junfeng Yang (State Key Laboratory of Green Chemical Synthesis and Conversion, Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China)

Abstract

Abstract This study reports a cobalt‐catalyzed method for the enantioselective reductive arylation and alkenylation of sulfinylamines, facilitating the efficient synthesis of enantiopure sulfinamides. By employing a cobalt/chiral diphosphine and tridentate ligand system, a range of diverse aryl and alkenyl iodides were successfully transformed into sulfinamides, achieving high yields and excellent enantioselectivity. This methodology underscores the utility of sulfinylamines as versatile electrophilic sulfur sources. Detailed mechanistic insights from density functional theory (DFT) calculations suggest that the key step involves migratory insertion into the sulfilimine group, which plays a crucial role in enantioselectivity. These findings offer a sustainable approach for the development of biologically relative enantiopure sulfur‐containing compounds.

Article Details

Volume / Issue Vol. 64, Issue 26
Published June 24, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (6)

Y

Yin Yuan

X

Xinyu Tian

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry

H

Hongxia Zheng

Department of Chemistry Fudan University 2205 Songhu Road Shanghai 200438 China

Y

Yuze Li

Heilongjiang Provincial Hospital

J

Junliang Zhang

Institute of Fuel Cells, School of Mechanical Engineering, MOE Key Laboratory of Power & Machinery Engineering

J

Junfeng Yang

State Key Laboratory of Green Chemical Synthesis and Conversion, Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China