Synthetic Applications of Photochemically Generated Radicals from Protic C(sp3)-H Bonds

The utilization of photo-induced processes in C-H functionalization via radical pathways has emerged as a highly promising strategy for the preparation and modification of complex organic compounds. While current methods for generating carbon-centred radicals from C-H bonds primarily focus on hydridic C-H bonds to yield nucleophilic radical species, the reactivity and potential applications of electrophilic radicals derived from protic C-H bonds remain largely unexplored. In this review, we aim to shed light on the seminal findings regarding the activation of protic C(sp(3))-H bonds while also showcasing noteworthy examples of this radical formation process. Mechanistically diverse modes of activation are discussed, unified by proton-coupled electron transfer (PCET) concepts.

Automated summary

The utilization of photo-induced processes in C-H functionalization via radical pathways has shown great potential for the preparation and modification of complex organic compounds. While current methods mainly focus on nucleophilic radicals derived from hydridic C-H bonds, the activation and potential applications of electrophilic radicals from protic C-H bonds remain largely unexplored. This review aims to highlight the important discoveries and showcase examples of protic C(sp(3))-H bond activation through mechanistically diverse modes unified by proton-coupled electron transfer (PCET) concepts.