Radical Cascade Reaction of Heterocyclic Ketene Aminals with Thiocyanates Promoted by Visible Light: Synthesis of Functionalized Fused 2-Iminothiazolines DOI

Shu Shu Yang,

Tingting Guo, Jianbo Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13678 - 13690

Published: Sept. 6, 2024

Herein, a visible-light-promoted radical cascade cyclization of heterocyclic ketene aminals (HKAs) and thiocyanates was developed to access functionalized fused 2-iminothiazolines. This novel reaction can be realized under only visible-light irradiation without the help external photocatalysts, oxidants, additives. These multicomponent reactions demonstrate excellent selectivity for

Language: Английский

Radical Rearrangement Reaction of Propargyl Ethers to α,β-Unsaturated Aldehydes via Photoredox and Ni Catalysis DOI
Qin Jiang,

Bi-Yin Xiao,

Wei Huang

et al.

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

Published: April 6, 2025

Aryl migration, especially 1,4-aryl is one of the most important reactions in radical rearrangement. Over past decades, migration by addition a to alkynes has become simple and efficient method difunctionalization alkynes. Radical-based aryl alkynoates been well-explored; however, propynyl ethers rarely studied. Herein, we first described propargyl ether valuable α,β-unsaturated aldehydes via photoredox Ni catalysis. This features redox-neutral conditions, readily available starting materials, broad substrate scope, good functional group compatibility, diverse transformations. Mechanistic studies suggest that this reaction proceeds through radical-involved pathway.

Language: Английский

Citations

0

Reactions of alkynes with C–S bond formation: recent developments DOI

Yuemei Xu,

Suhang Zhang, Dayun Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6443 - 6484

Published: Jan. 1, 2024

Alkynes are important in organic synthesis. This review mainly focuses on the recent advances (2013–2023) alkynes with C–S bond formation, based more than 30 kinds of sulfur reagents.

Language: Английский

Citations

2

Visible-Light-Driven Synthesis of Alkenyl Thiocyanates: Novel Building Blocks for Diverse Sulfur-Containing Molecular Assembly DOI Creative Commons
Helena F. Piedra, Manuel Plaza

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A new photochemical method to prepare alkenyl thioethers under both batch and continuous flow conditions is presented. These versatile building blocks enable the synthesis of various organosulfur compounds, highlighting utility this procedure.

Language: Английский

Citations

1

A Continuous Flow Protocol for the Synthesis of Alkenyl Thioethers Based on the Photochemical Activation of Halogen-Bonding Complexes DOI
Manuel Plaza, Helena F. Piedra, Carlos Valdés

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: June 15, 2024

Abstract We report a useful flow protocol for the preparation of alkenyl thioethers from bromides and thiols in basic media with visible-light irradiation. The reactions exhibit wide functional-group tolerance, proceed under mild conditions, are stereoselective, do not require use catalysts. transformations can be successfully scaled up to 5 mmol scale without compromising yield. key success these is photochemical excitation halogen-bonding complexes form sulfur-centered radicals, recently developed our laboratories.

Language: Английский

Citations

0

Radical Cascade Reaction of Heterocyclic Ketene Aminals with Thiocyanates Promoted by Visible Light: Synthesis of Functionalized Fused 2-Iminothiazolines DOI

Shu Shu Yang,

Tingting Guo, Jianbo Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13678 - 13690

Published: Sept. 6, 2024

Herein, a visible-light-promoted radical cascade cyclization of heterocyclic ketene aminals (HKAs) and thiocyanates was developed to access functionalized fused 2-iminothiazolines. This novel reaction can be realized under only visible-light irradiation without the help external photocatalysts, oxidants, additives. These multicomponent reactions demonstrate excellent selectivity for

Language: Английский

Citations

0