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Visible-Light-Driven α-Aminoalkyl Radical-Mediated C(sp<sup>3</sup>)–C(sp) Cross-Coupling of Iodoalkanes and Alkynyl Bromides

Alisha Rani Tripathy, Amit Kumar, Rizwana Rahmathulla A, Avishek Kumar Jha, Veera Reddy Yatham

2022Organic Letters27 citationsDOI

Abstract

We herein report a simple protocol for metal-free cross-coupling between unactivated alkyl iodides and terminal alkynyl bromides promoted by visible light. The salient features of this transformation are the utilization of an organic photocatalyst and commercially available tri-n-butylamine as a reductant. This protocol couples a variety of unactivated iodoalkanes containing different functional groups and with a variety of terminal alkynyl bromides under mild reaction conditions to afford the substituted alkynes in good yields.

Topics & Concepts

ChemistryAlkylVisible spectrumCoupling reactionPhotochemistryCombinatorial chemistryMedicinal chemistryCatalysisOrganic chemistryPhysicsOptoelectronicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions
Visible-Light-Driven α-Aminoalkyl Radical-Mediated C(sp<sup>3</sup>)–C(sp) Cross-Coupling of Iodoalkanes and Alkynyl Bromides | Litcius