Work

Asymmetric S ‐Arylation of Sulfenamides to Access Axially Chiral Sulfilimines Enabled by Anionic Stereogenic‐at‐Cobalt(III) Complexes

Year: 2024

Type: article

Abstract: An efficient enantioselective coupling reaction between sulfenamides and cyclic diaryliodonium salts is established via adaptive Cu/anionic stereogenic-at-Co(III) complex combined catalysis, precisely synthesizing a broad range of axially chiral sulfilimines with excellent enantioselectivities, diastereoselectivities, regioselectivities, and chemoselectivities (67 examples under same conditions, up to 98 % ee). The following thermodynamically controlled pyramidal inversion enables efficient stereodivegent synthesis of all four stereoisomers. Mechanistic studies suggest that anionic stereogenic-at-cobalt(III) complexes serve as counteranions of diaryliodonium and anionic ligand of Cu(I) catalyst simultaneously, which could be regarded as an explanation for outstanding selectivities.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202419596

Authors: Wei Fang, Yan‐Dong Meng, Shu‐Ying Ding, Ju‐Yan Wang, Zheng‐Hao Pei, Meng‐Lan Shen, Chuan‐Zhi Yao, Qiankun Li, Zhenhua Gu, Jie Yu, Hua‐Jie Jiang

Institutions: Anhui Agricultural University, University of Science and Technology of China, Nanjing University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Anhui Agricultural University, Natural Science Foundation of Anhui Province

Awards: G3446949044, G3781650882, G4786685163, G6236122997

OpenAlex ID: W4404964379

FWCI: 8.328

Cites: 94

Cited by: 60

Related to: 10