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Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones

Simon L. Homölle, Maximilian Stangier, Efraím Reyes, Lutz Ackermann

2023Precision Chemistry12 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide While electrocatalyzed alkyne annulations of arenes represent a powerful strategy for the assembly of heteroaromatic motives, electrochemical C(sp 2 )–H activations of alkenes remain scarce. Herein, a strategy for the rhodaelectro-catalyzed functionalization of enamides is presented for the efficient construction of pyrroles using electricity as a sustainable oxidant. Moreover, the tuning of the solvent system allowed a fascinating switch in chemoselectivity, which is not possible with traditionally used chemical oxidants, giving rise to lactone architectures. The rhoda-electrocatalysis features a broad scope as well as high regio- and chemoselectivities.

Topics & Concepts

ChemoselectivityCatalysisAlkyneChemistryScope (computer science)Combinatorial chemistryElectrocatalystElectrochemistryOrganic chemistryComputer sciencePhysical chemistryElectrodeProgramming languageCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones | Litcius