Catalyst‐Free Deaminative Functionalizations of Primary Amines by Photoinduced Single‐Electron Transfer

作者：Jingjing Wu, Phillip Grant, Xiabing Li, Adam Noble, Varinder K. Aggarwal · 发表于：Angewandte Chemie · 年份：2019 · DOI：10.1002/ange.201814452 · 被引用次数：64 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Sulfur-Based Synthesis Techniques

Abstract The use of pyridinium‐activated primary amines as photoactive functional groups for deaminative generation of alkyl radicals under catalyst‐free conditions is described. By taking advantage of the visible light absorptivity of electron donor–acceptor complexes between Katritzky pyridinium salts and either Hantzsch ester or Et 3 N, photoinduced single‐electron transfer could be initiated in the absence of a photocatalyst. This general reactivity platform has been applied to deaminative alkylation (Giese), allylation, vinylation, alkynylation, thioetherification, and hydrodeamination reactions. The mild conditions are amenable to a diverse range of primary and secondary alkyl pyridiniums and demonstrate broad functional group tolerance.