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

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
Modular construction of sulfinimidate esters: expanding chemical space and enabling late-stage diversification DOI
Ruyi Li,

Huaqin Wu,

Hang Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3881 - 3893

Published: Jan. 1, 2024

We have successfully developed a versatile approach for synthesizing sulfinimidate esters, by making use of thiols, amines, and alcohols.

Language: Английский

Citations

1
Halogen-Free Bleaching of Shellac Using Electrochemically Generated Peroxodicarbonate DOI Creative Commons
Tomas Horsten, Siegfried R. Waldvogel

RSC Sustainability, Journal Year: 2024, Volume and Issue: 2(7), P. 1963 - 1968

Published: Jan. 1, 2024

A halogen-free bleaching of shellac was developed using electrochemically generated peroxodicarbonate with acetonitrile as an activator. reduced damage is obtained compared to previous reports.

Language: Английский

Citations

1
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

1