A General Nitrene Transfer to Sulfides Enabled by Visible-Light-Mediated Triplet Energy Transfer to Sulfonyl Azides DOI Creative Commons
Norihito Arichi,

Tsuyoshi Amano,

Shuhan Wu

et al.

Published: April 10, 2024

Sulfilimines and their derivatives have garnered considerable interest in both synthetic medicinal chemistry. Photochemical nitrene transfer to sulfides is known as a conventional approach sulfilimines. However, the existing methods limited substrate scope stemming from incompatibility of singlet intermediates with nucleophilic functional groups. Herein, we report general for synthesis N-sulfonyl sulfilimines enabled by visible-light-mediated energy sulfonyl azides, uncovering neglected reactivity triplet nitrenes sulfides. The unprecedented mechanism involving single electron broad group tolerance, water compatibility, amenability use late-stage functionalization drugs.

Language: Английский

Photocatalytic Nitrene Radical Anion Generation from Sulfonyl Azides for Intermolecular Aziridination of Unactivated Alkenes DOI Creative Commons
Dennis Dam,

Joeri Schoenmakers,

Elisabeth Bouwman

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 3, 2025

Aziridines are important structures in the contemporary organic synthesis and used for several biological applications. Herein, we show that aziridines can be readily synthesized from alkenes by reductive activation of sulfonyl azides, mediated photoredox catalysis. Mechanistic studies indicate reaction proceeds through reactive nitrene radical anions instead more commonly encountered triplet nitrenes. A substrate scope is performed showed good functional group compatibility.

Language: Английский

Citations

0
Combined Synthetic, Spectroscopic, and Computational Insights Into a General Method for Photosensitized Alkene Aziridination DOI
Alana Rose Meyer, Mihai V. Popescu, Arindam Sau

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 12310 - 12317

Published: Aug. 2, 2024

Aziridines are important targets for synthetic chemistry, and many methods involving the aziridination of alkenes by olefins with nitrenes have been reported. In general, however, nitrene transfer reactions optimized a limited range precursors, synthesis structurally diverse aziridines featuring N-substituents requires application multiple varying reaction conditions. Herein, we report photocatalytic method that operates wide N-substituted precursors. A combination synthetic, spectroscopic, computational data is consistent mechanism generation triplet intermediates. The effectiveness 4DPAIPN as photocatalyst this process can be rationalized consequence its exceptionally long lifetime, rather than excited state energies or redox properties in isolation.

Language: Английский

Citations

3
Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art DOI
Lucas G. Furniel, Arlene G. Corrêa

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(9)

Published: May 13, 2024

Abstract The development of greener methods for the preparation three‐membered rings has increased in last decade, not only due to their biological activity but also ring strain those heterocycles that make them useful precursors more complex molecules. In this work, visible‐light‐promoted synthesis and ring‐opening aziridines epoxides, reported five years, were reviewed. Both homogeneous heterogeneous catalysts discussed and, addition, plausible mechanism pathways highlighted.

Language: Английский

Citations

2
Synthesis of Sulfilimines via Visible‐Light‐Mediated Triplet Energy Transfer to Sulfonyl Azides DOI
Norihito Arichi,

Tsuyoshi Amano,

Shuhan Wu

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(48)

Published: June 24, 2024

Abstract Sulfilimines and their derivatives have garnered considerable interest in both synthetic medicinal chemistry. Photochemical nitrene transfer to sulfides is known as a conventional approach sulfilimines. However, the existing methods limited substrate scope stemming from incompatibility of singlet intermediates with nucleophilic functional groups. Herein, we report synthesis N ‐sulfonyl sulfilimines via visible‐light‐mediated energy sulfonyl azides, uncovering previously overlooked reactivity triplet nitrenes sulfides. This reaction features broad group tolerance, water compatibility, amenability late‐stage functionalization drugs. Thus, this work represents an important example chemistry that overcomes challenges traditional methods.

Language: Английский

Citations

2
A General Nitrene Transfer to Sulfides Enabled by Visible-Light-Mediated Triplet Energy Transfer to Sulfonyl Azides DOI Creative Commons
Norihito Arichi,

Tsuyoshi Amano,

Shuhan Wu

et al.

Published: April 9, 2024

Sulfilimines and their derivatives have garnered considerable interest in both synthetic medicinal chemistry. Photochemical nitrene transfer to sulfides is known as a conventional approach sulfilimines. However, the existing methods limited substrate scope stemming from incompatibility of singlet intermediates with nucleophilic functional groups. Herein, we report general for synthesis N-sulfonyl sulfilimines enabled by visible-light-mediated energy sulfonyl azides, uncovering neglected reactivity triplet nitrenes sulfides. The unprecedented mechanism involving single electron broad group tolerance, water compatibility, amenability use late-stage functionalization drugs.

Language: Английский

Citations

1
A General Nitrene Transfer to Sulfides Enabled by Visible-Light-Mediated Triplet Energy Transfer to Sulfonyl Azides DOI Creative Commons
Norihito Arichi,

Tsuyoshi Amano,

Shuhan Wu

et al.

Published: April 10, 2024

Sulfilimines and their derivatives have garnered considerable interest in both synthetic medicinal chemistry. Photochemical nitrene transfer to sulfides is known as a conventional approach sulfilimines. However, the existing methods limited substrate scope stemming from incompatibility of singlet intermediates with nucleophilic functional groups. Herein, we report general for synthesis N-sulfonyl sulfilimines enabled by visible-light-mediated energy sulfonyl azides, uncovering neglected reactivity triplet nitrenes sulfides. The unprecedented mechanism involving single electron broad group tolerance, water compatibility, amenability use late-stage functionalization drugs.

Language: Английский

Citations

1