Electrochemically Induced Synthesis of Substituted 5-Thiotetrazoles DOI
Feng Zhao, Bin Song,

Pengxiang Gao

et al.

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

Published: May 6, 2025

A novel electrochemical procedure for the one-pot synthesis of variously substituted 5-thiotetrazole has been established by a three-component reaction (thiol(thiophenol)s, isocyanides, and azidotrimethylsilane). This approach is achieved sulfidation isocyanide subsequent cycloaddition with azidotrimethylsilane under mild conditions without metal catalyst or external oxidant. Importantly, presented methodology not only features wide substrate scope but also exhibits practicality showcased gram-scale various conversions.

Language: Английский

Energy Transfer (EnT)-Mediated Stereoselective Aryl-Heterofunctionalization of Unactivated Alkynes via Radical Rearrangement DOI

Xin-Chao Meng,

Tai‐Long Pan,

Feng Yang

et al.

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

Published: Jan. 5, 2025

In this study, we present a novel catalyst-free energy transfer mediated radical rearrangement strategy for the aryl-heterofunctionalization of unactivated alkynes, leading to synthesis polyfunctional olefins with exceptional stereoselectivity. This innovative approach, driven by visible light, exemplifies green chemistry principles eliminating reliance on transition metals, external oxidants, and photocatalysts. The broad applicability our method is demonstrated through successful diverse array compounds, including vinyl sulfones, selenides, sulfides. Preliminary mechanistic insights suggest an mechanism, highlighting efficiency selectivity strategy.

Language: Английский

Citations

0
Metal-Free Visible-Light Excitation of TMSN3 Enables [3 + 2] Cycloaddition of Arylidenecyclopropanes with Olefins DOI
Yayu Wang,

Ting-Feng Fu,

Xiao Hu

et al.

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

Published: April 14, 2025

A visible-light photoredox [3 + 2] cycloaddition reaction of arylidenecyclopropanes with olefins was developed, employing the readily available and commercially accessible TMSN3 as an efficient radical mediator. This method provides a convenient route to arylidenecyclopentanes from starting materials, is metal-free, features enhanced atom step economy, excellent selectivity, extensive substrate versatility, favorable functional group compatibility, structural diversity, mild conditions, which further enable late-stage diversification. DFT calculations elucidated that this transformation entails sequential generation, addition, ring-opening, cyclization, elimination steps.

Language: Английский

Citations

0
Electrochemically Induced Synthesis of Substituted 5-Thiotetrazoles DOI
Feng Zhao, Bin Song,

Pengxiang Gao

et al.

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

Published: May 6, 2025

A novel electrochemical procedure for the one-pot synthesis of variously substituted 5-thiotetrazole has been established by a three-component reaction (thiol(thiophenol)s, isocyanides, and azidotrimethylsilane). This approach is achieved sulfidation isocyanide subsequent cycloaddition with azidotrimethylsilane under mild conditions without metal catalyst or external oxidant. Importantly, presented methodology not only features wide substrate scope but also exhibits practicality showcased gram-scale various conversions.

Language: Английский

Citations

0