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

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.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-04-27
DOI
https://doi.org/10.1002/anie.202506243
Citations
23
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
21.53
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article

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

Junfeng Yang, Yin Yuan, Yuze Li, Xinyu Tian et al.
23 citations
Angewandte Chemie International Edition
Catalytic C–H Functionalization Methods
21.53
article

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

Junfeng Yang, Yin Yuan, Yuze Li, Xinyu Tian, Hongxia Zheng, Junliang Zhang
article en
23 citations

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.

Angewandte Chemie International EditionVol. 64(26)
Fudan University (CN), Zhengzhou University (CN), Henan Normal University (CN), Yangzhou University (CN)
Openalex Percentile: Top 0%
Catalytic C–H Functionalization Methods
21.53
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