Work

Ruthenaphoto-catalyzed ortho-C−H alkylation with secondary alkyl halides: SET-enabled ruthenium(II/III/IV) manifold

Year: 2024

Type: article

Abstract: The activation of organic halides by transition metals is one of the most important elementary processes in organic synthesis, which can be achieved by a two-electron oxidation addition process or a one-electron radical process. Currently, the ruthenium-catalyzed meta -C(sp 2 )–H alkylation with alkyl halides has emerged as a robust tool for remote C(sp 2 )–H functionalization and was unambiguously proved to occur via a radical pathway. By contrast, the modus operandi of ruthenium-catalyzed ortho -C(sp 2 )–H alkylation is still somewhat unclear and was proposed to occur through a two-electron manifold of ruthenium(II/IV) regime. In this context, we reported on a photo-induced ruthenium-catalyzed ortho -C(sp 2 )−H alkylation with secondary/primary alkyl bromides. Mechanistic studies by experiment and computation provide strong support for a ruthenium(II/III/IV) regime, involving a SET between alkyl bromide and the in situ -generated bicycloruthenated complex.

Source: Chem

DOI: 10.1016/j.chempr.2024.12.005

Authors: Yulei Wang, Binbin Yuan, Xuexue Chang, Lutz Ackermann

Institutions: University of Göttingen, Nanjing University, German Centre for Cardiovascular Research

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $9,350