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

N‐Hydroxyphthalimide/TiO2 Catalyzed Addition of Ethers, Alkylarenes and Aldehydes to Azodicarboxylates under Visible Light DOI Open Access
Elena R. Lopat’eva, Igor B. Krylov, Alexander O. Terent’ev

et al.

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

The addition of carbon-centered radicals to double bonds is one the most atom-efficient approaches formation new C-C or C-heteroatom bonds. Existing for generation often require elevated temperatures, UV radiation expensive transition metal catalysts. In this work, a photocatalytic system based on heterogeneous TiO2 catalyst and redox organocatalyst N-hydroxyphthalimide proposed from C(sp3)-H substrates aldehydes at room temperature under visible light irradiation. developed approach was successfully applied ethers, alkylarenes azodicarboxylates. Titanium oxide acts as photocatalyst, producing phthalimide-N-oxyl N-hydroxyphthalimide, thereby enabling organocatalytic process in solution. Phthalimide-N-oxyl act catalytically active species that cleave C-H form radicals.

Language: Английский

Citations

2
Radical Brook rearrangement: past, present, and future DOI
Yunxiao Zhang, Gang Zhou, Shanshan Liu

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review aims to provide an overview of radical Brook rearrangement, which is organized by grouping three type reactive species generated via the unique rearrangement process.

Language: Английский

Citations

1
Photocatalytic Oxidative Hydroacylation with Alcohols DOI

Sabhya Sandha,

Chandra Bhushan Tripathi

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A photocatalytic oxidative hydroacylation with alcohols for C–N and C–C bond formation is reported.

Language: Английский

Citations

0
Visible-Light-Induced Insertion of Siloxycarbene into Amide N–H Bonds: Synthesis of Carbinolamides from Acylsilanes and Amides DOI

Praveen Dharavath,

Raju Vaggu,

Manda Rajesh

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1727 - 1732

Published: Jan. 20, 2025

The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced siloxycarbene bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions a broad range amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable N- O-acetals excellent isolated yields. addition, chemoselective reveals robustness chemical transformation.

Language: Английский

Citations

0
Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones DOI
Pokhriyal Yamini, Akanksha Babbar, Dongari Yadagiri

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 6035 - 6040

Published: July 10, 2024

Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report light-driven intramolecular cyclopropanation alkene-tethered

Language: Английский

Citations

2
Light-Induced Reactivity of Nucleophilic Siloxycarbene with Heterocumulenes: Synthesis of α-Ketoamides, Hydantoins, Oxoacetamidines, and Amides DOI
Mohammad Saleem,

Pandey Abhishek,

Dongari Yadagiri

et al.

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

Published: Nov. 25, 2024

We report the reactivity of in situ-generated nucleophilic siloxycarbenes from acylsilanes via 1,2-Brook rearrangement presence visible light with heterocumulenes. This method significantly advances conventional use electrophilic carbenes stabilized by metal catalysts and harsh reaction conditions. The was explored isocyanates, carbodiimides,

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

0