Strategic Synthesis of Sulfinamides as Versatile S(IV) Intermediates DOI Creative Commons
Subham Das,

Amit Dhibar,

Basudev Sahoo

et al.

ACS Organic & Inorganic Au, Journal Year: 2024, Volume and Issue: 5(1), P. 1 - 12

Published: Nov. 30, 2024

Sulfinamides constitute adaptable S(IV) intermediates with a sulfur stereocenter, having emerging interest in divergent synthesis of high-valent S(VI) functional bioisosteres. Recent years have witnessed the strategic development mild and selective synthetic routes for highly functionalized sulfinamides, employing stable organometallic reagents, carbon-centered radical precursors, other abundant coupling partners merged various reagents arena metal, photoredox, organocatalysis. Furthermore, asymmetric metal organocatalysis enabled stereoselective enantioenriched sulfinamides. In this Perspective, we present recent (2021 to present) advancement methods toward

Language: Английский

Sulfilimines: An Underexplored Bioisostere for Drug Design? DOI Creative Commons
Per I. Arvidsson

Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Sulfilimines have so far received little attention as a bioisostere for sulfoxides in the design of biologically active compounds. A recent study on physicochemical and vitro drug-like properties shows that sulfilimines deserve place medicinal chemist's toolbox.

Language: Английский

Citations

2
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
Visible-Light-Mediated Copper-Catalyzed S-Arylation of Sulfenamides with Aryl Thianthrenium Salts DOI
Xiangyu Zhuang, Hao Li,

Zhaoyu Feng

et al.

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

Published: May 2, 2025

The site-selective incorporation of sulfilimine functionalities into aromatic compounds provides a vital strategy for drug discovery in medicinal chemistry. However, green and sustainable methods realizing the goal are still limited. Here, we report copper-catalyzed S-arylation sulfenamides with aryl thianthrenium salts irradiated by visible light without photocatalyst, which exhibited fine functional-group compatibility gave desired products high yields. Mechanistic investigations revealed that key to achieving these results is generation an electron donor-acceptor (EDA) complex between under basic conditions.

Language: Английский

Citations

0
Synthesis of Sulfenamides via Photoredox N–S Coupling of Dialkyl Azodicarboxylates and Thiols DOI
Qun Liu,

Xiaoyun Feng,

Fang Xie

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 27, 2024

We herein report a photoredox N–S coupling reaction between dialkyl azodicarboxylates and thiols to access sulfenamide scaffolds. This proceeds under mild, green, operationally simple conditions, offering broad scope of sulfenamides with high yields excellent atom efficiency. Mechanistic investigations revealed this followed photoinitiated radical pathway in which iodide plays crucial role as both initiator single-electron reductant.

Language: Английский

Citations

2
Strategic Synthesis of Sulfinamides as Versatile S(IV) Intermediates DOI Creative Commons
Subham Das,

Amit Dhibar,

Basudev Sahoo

et al.

ACS Organic & Inorganic Au, Journal Year: 2024, Volume and Issue: 5(1), P. 1 - 12

Published: Nov. 30, 2024

Sulfinamides constitute adaptable S(IV) intermediates with a sulfur stereocenter, having emerging interest in divergent synthesis of high-valent S(VI) functional bioisosteres. Recent years have witnessed the strategic development mild and selective synthetic routes for highly functionalized sulfinamides, employing stable organometallic reagents, carbon-centered radical precursors, other abundant coupling partners merged various reagents arena metal, photoredox, organocatalysis. Furthermore, asymmetric metal organocatalysis enabled stereoselective enantioenriched sulfinamides. In this Perspective, we present recent (2021 to present) advancement methods toward

Language: Английский

Citations

1