Metal-Free Visible-Light Excitation of TMSN₃ Enables [3 + 2] Cycloaddition of Arylidenecyclopropanes with Olefins

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

Nickel/ligand loading-controlled divergent and selective coupling between redox-active methylenecyclopropanes and ArBr

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5720 - 5730

Published: Jan. 1, 2024

Diverse alkyne and dibenzylethylene derivatives were obtained via selective coupling of redox-active MCPs ArBr under Ni/photoredox catalysis. The nickel/ligand loading tuning method played a crucial role in this divergent synthesis protocol.

Language: Английский