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Electron Donor‐Acceptor (EDA) Complex Enabled C−C Cross‐Coupling Reactions of α‐Amino Radicals

Padmanava Barik, Subhra Sriharsa Behera, Santosh K. Nanda

2024Asian Journal of Organic Chemistry19 citationsDOI

Abstract

Abstract Electron‐donor acceptor (EDA) complex has been an integral part of visible‐light photocatalysis and is different from the traditional photoredox catalysis, which requires an exogenous photocatalyst, typically a colored compound to initiate the photocatalytic cycle. Interestingly, the EDA‐complex photochemistry has found profound use in activating the inert α‐C−H bonds of amines. The strategy relied upon the formation of colored EDA‐complex between the donor (amine) and acceptor (Lewis acid), which upon harvesting light energy perform a SET process to generate radical cation and anion intermediates. The radical cation then loses the activated acidic proton (because of the SET, the acidity of α‐proton increases by lowering the BDE) to form α‐amino radical, which then participates in various C−C coupling cascades. In this review, different conceptual approaches for the generation of α‐amino radicals and their coupling for the C−C bond‐forming reaction under EDA‐complex triggered photocatalysis will be discussed with particular emphasis on the reaction mechanism from 2018 onwards.

Topics & Concepts

ChemistryRadicalAcceptorElectron acceptorCoupling (piping)ElectronPhotochemistryCoupling reactionStereochemistryComputational chemistryOrganic chemistryCatalysisPhysicsCondensed matter physicsEngineeringQuantum mechanicsMechanical engineeringRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods
Electron Donor‐Acceptor (EDA) Complex Enabled C−C Cross‐Coupling Reactions of α‐Amino Radicals | Litcius