Cu-Catalyzed Enantioselective S-Arylation of Sulfenamides Enabled by Confined Ligands DOI
Xiaobao Wu,

Yue Shen,

Hua‐Jie Jiang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Chiral sulfilimines, aza analogues of sulfoxides, are essential in natural products and pharmaceuticals, highlighting the importance their synthesis asymmetric catalysis. However, efficient approaches for synthesizing chiral diaryl sulfilimines still rare challenging, particularly those with two sterically similar aryl groups. Herein, we present a mild protocol generating diverse enantioenriched alkyl via copper-catalyzed enantioselective S-arylation N-acyl sulfenamides diaryliodonium salts. A bulky PyBox ligand is crucial stereocontrol, delivering various up to 95% ee (51 examples).

Language: Английский

Dual Copper/Photoredox Catalysis for Radical-Mediated Arylation and Alkylation of Sulfenamides DOI
Mingjun Zhang,

Yuhao Tan,

Hehe Yang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4007 - 4016

Published: Feb. 20, 2025

Language: Английский

Citations

0
Anionic Stereogenic-at-Cobalt(III) Complex-Enabled Asymmetric Oxidation of N,N-Dialkyl Sulfenamides DOI

Yue Shen,

Xiaobao Wu,

Hua‐Jie Jiang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 26, 2025

An asymmetric oxidation of N,N-dialkyl sulfenamides is exhibited by using anionic stereogenic-at-cobalt(III) complexes as catalysts. This protocol provides an alternative approach to access a diverse set chiral tertiary sulfinamides with high enantioselectivities (24 examples, up 94:6 e.r.). Additionally, control experiments suggest that this could be accomplished through cationic S(IV) intermediate.

Language: Английский

Citations

0
Regioselective N-arylation of N-Acylsulfenamides Enabled by o-Quinone Diimides DOI
Xuebin Yan, Rui Zhao, Yu‐Hang Miao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

The functionalization of N-acylsulfenamides is a research focus in organosulfur chemistry, as the N-S array has unique properties and versatile applications. Although great progress been made S-functionalization, N-functionalization, especially N-arylation N-acylsulfenamides, rarely explored because lower nucleophilicity N-site. Herein, we report Brønsted acid-catalyzed regioselective reaction with o-quinone diimides. Under mild metal-free conditions, wide range N-arylated have prepared good yields excellent regioselectivity. ease gram-scale synthesis transformations into useful sulfonamides demonstrates their synthetic practicality.

Language: Английский

Citations

0
Assembly of (Hetero)aryl Sulfoximines via Copper-Catalyzed S-Arylation of Sulfinamides with (Hetero)aryl Halides DOI
Mingchuang He,

Rongxing Zhang,

Dawei Ma

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 18, 2025

The combination of CuI and 4-(dimethylamino)picolinamide offers an effective catalytic system for the successful coupling (hetero)aryl halides (I Br) with sulfinamides first time. A large number functional groups heterocycles were tolerated under conditions, providing a powerful approach diverse synthesis pharmaceutically important sulfoximines. efficiency reaction was highly dependent upon electronic nature substituents at amide part sulfinamides. By using enantioenriched as partners, proceeds in stereospecific manner to afford sulfoximines excellent enantioselectivity.

Language: Английский

Citations

0
Cu-Catalyzed Enantioselective S-Arylation of Sulfenamides Enabled by Confined Ligands DOI
Xiaobao Wu,

Yue Shen,

Hua‐Jie Jiang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Chiral sulfilimines, aza analogues of sulfoxides, are essential in natural products and pharmaceuticals, highlighting the importance their synthesis asymmetric catalysis. However, efficient approaches for synthesizing chiral diaryl sulfilimines still rare challenging, particularly those with two sterically similar aryl groups. Herein, we present a mild protocol generating diverse enantioenriched alkyl via copper-catalyzed enantioselective S-arylation N-acyl sulfenamides diaryliodonium salts. A bulky PyBox ligand is crucial stereocontrol, delivering various up to 95% ee (51 examples).

Language: Английский

Citations

0