Hydride shift mediated C(sp3)-H bond functionalization starting from non-aniline/phenol type substrates: Evolution into a sequential system

Hydride shift mediated C(sp(3))-H bond functionalization, namely, internal redox reaction, is an useful synthetic tool for the construction of fused cycles. Most of the reactions reported so far have focused on the reactions with aniline and phenol derivatives (a heteroatom is directly connected to an aromatic ring), and reactions using substrates having a carbon linker between the aromatic ring and the heteroatom have been overlooked. Recently, various novel reactions starting from the latter type of substrates have been developed, paving the way for new opportunities for the internal redox reaction. In this digest, we summarize recent progress in internal redox reactions that have enabled the unprecedented double C (sp(3))-H bond functionalization, the combination of other organic transformations, and the construction of a medium-sized ring. (C) 2022 Elsevier Ltd. All rights reserved.

Automated summary

Hydride shift mediated C(sp(3))-H bond functionalization is a useful synthetic tool for constructing fused cycles. Most studies have focused on reactions with aniline and phenol derivatives, while reactions using substrates with a carbon linker between the aromatic ring and the heteroatom have been overlooked. Recently, various novel reactions starting from these substrates have been developed.