Heteroarylation of Sulfenamides for Modular Synthesis of Antimicrobial Sulfilimines via Sulfinimidoyl Fluoride Intermediates DOI

Chunyan Jian,

Xuan Huang,

Hongyan Long

et al.

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

Published: May 20, 2025

We herein disclose a mild metal-free strategy for the construction of heteroaryl-derived sulfilimines. Central to this approach is in situ generated sulfinimidoyl fluoride intermediate that exhibits an optimal balance reactivity and stability efficient S(IV)-derived SuFEx reactions with heteroarenes without Lewis acids or base additives. This protocol enables rapid incorporation broad range afford diverse sulfilimine scaffolds potent antimicrobial activities against plant pathogens.

Language: Английский

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
Mechanochemical syntheses of N-acyl sulfinamidines via iron-nitrenoids and their conversions to sulfur(VI) derivatives DOI Creative Commons

Shulei Pan,

Peng Wu, Yijie Hu

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0
Ruthenium-Catalyzed Enantioselective Alkylation of Sulfenamides: A General Approach for the Synthesis of Drug Relevant S-Methyl and S-Cyclopropyl Sulfoximines DOI

Zachary W. Boyer,

Na Yeon Kwon, Jonathan A. Ellman

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Sulfoximines are increasingly utilized in pharmaceuticals and agrochemicals with all sulfoximine clinical candidates incorporating either an S-methyl or S-cyclopropyl substituent. Here, we report on a general efficient sequence for the asymmetric synthesis of both these substitution patterns. The sulfilimine intermediates by first Ru-catalyzed enantioselective alkylation sulfenamides enables examples S-alkylation monosubstituted diazo compounds. reaction proceeds at ≤1 mol % Ru-catalyst loading, tert-butyl diazoacetate, high yields ≥98:2 er achieved exceedingly broad range sulfenamides, including S-(hetero)aryl, -alkenyl, -methyl, -benzyl, -branched alkyl, -tert-butyl substituents sterically electronically diverse N-acyl groups. Sulfenamides derived from densely functionalized advanced drug also alkylated 99:1 er. After oxidation N-pivaloyl S-tert-butyl acetate substituted to corresponding sulfoximine, treatment trifluoracetic acid aprotic solvent resulted decarboxylation while aqueous HCl cleavage group give NH sulfoximine. Alternatively, dibromoethane followed acid-mediated provided preclinical candidate LTGO-33 formal phase II ART0380 demonstrate utility disclosed approach.

Language: Английский

Citations

0
Heteroarylation of Sulfenamides for Modular Synthesis of Antimicrobial Sulfilimines via Sulfinimidoyl Fluoride Intermediates DOI

Chunyan Jian,

Xuan Huang,

Hongyan Long

et al.

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

Published: May 20, 2025

We herein disclose a mild metal-free strategy for the construction of heteroaryl-derived sulfilimines. Central to this approach is in situ generated sulfinimidoyl fluoride intermediate that exhibits an optimal balance reactivity and stability efficient S(IV)-derived SuFEx reactions with heteroarenes without Lewis acids or base additives. This protocol enables rapid incorporation broad range afford diverse sulfilimine scaffolds potent antimicrobial activities against plant pathogens.

Language: Английский

Citations

0