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Three-Component Aminoheteroarylation of Alkenes via Photoinduced EDA Complex Activation

Chengcheng Shi, Lin Guo, Han Gao, Mengqi Luo, Xiao Zhou, Chao Yang, Wujiong Xia

2023Organic Letters33 citationsDOI

Abstract

A catalyst-free approach for the multicomponent aminoheteroarylation reaction of alkenes with N -aminopyridinium salts and heteroarenes is herein described. The reaction shows good functional group tolerance and allows the generation of valuable β-heteroarylethylamines in satisfying yields. In this transformation, N -aminopyridinium salts and heteroarenes are utilized to generate electron donor–acceptor complexes, which undergo a single-electron transfer process upon light irradiation to form key amidyl radicals and heteroaryl radical cations. The amidyl radical is subsequently captured by alkenes, followed by a Minisci-type reaction to yield the desired β-heteroarylamines as products.

Topics & Concepts

ChemistryComponent (thermodynamics)Combinatorial chemistryThermodynamicsPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Three-Component Aminoheteroarylation of Alkenes via Photoinduced EDA Complex Activation | Litcius