Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy

2020/08/06 by Stefano Crespi, Maurizio Fagnoni · 3 citations
Chemistry · #Catalytic C–H Functionalization Methods #Radical Photochemical Reactions #Sulfur-Based Synthesis Techniques

paper · pdf · doi:10.1021/acs.chemrev.0c00278

openalex publication_date 2020/08/06 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30

Abstract

Alkyl radicals are key intermediates in organic synthesis. Their classic generation from alkyl halides has a severe drawback due to the employment of toxic tin hydrides to the point that "flight from the tyranny of tin" in radical processes was considered for a long time an unavoidable issue. This review summarizes the main alternative approaches for the generation of unstabilized alkyl radicals, using photons as traceless promoters. The recent development in photochemical and photocatalyzed processes enabled the discovery of a plethora of new alkyl radical precursors, opening the world of radical chemistry to a broader community, thus allowing a new era of photon democracy.

Citations

• Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides

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