Metal-Free, Visible-Light-Induced Remote C(sp3)-H Pyridylation via Radical Translocation of N-Alkoxypyridinium Salts.

Metal-Free, Visible-Light-Induced Remote C(sp3)-H Pyridylation via Radical Translocation of N-Alkoxypyridinium Salts. Angew Chem Int Ed Engl. 2018 Oct 02;: Authors: Kim I, Park B, Kang G, Kim J, Jung H, Lee H, Baik MH, Hong S Abstract Metal-free, visible-light-induced site-selective heteroarylation of remote C(sp3)-H bonds has been accomplished through the design of N-alkoxyheteroarenium salts serving as both alkoxy radical precursors and heteroaryl sources. The transient alkoxy radical can be generated via the single electron reduction of an N-alkoxypyridinium substrates by a photoexcited quinolinone catalyst. Subsequent radical translocation of the alkoxy radical forms a nucleophilic alkyl radical intermediate, which undergoes addition to the substrate to achieve remote C(sp3)-H heteroarylation. This cascade strategy provides a powerful platform for remote C(sp3)-H heteroarylation in a controllable and selective manner and is well suited for late-stage functionalization of complex bioactive molecules. PMID: 30277296 [PubMed - as supplied by publisher]
Source: Angewandte Chemie - Category: Chemistry Authors: Tags: Angew Chem Int Ed Engl Source Type: research