Photoredox/Nickel Dual Catalysis Enables the Synthesis of Alkyl Cyclopropanes via C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross Electrophile Coupling of Unactivated Alkyl Electrophiles
Sayan K. Jana, Mamata Maiti, Purusattam Dey, Biplab Maji
Abstract
A facile synthesis of mono-, 1,1- and 1,2-disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis is demonstrated. The challenging intramolecular C(sp3)–C(sp3) cross-electrophile coupling of readily available unactivated 1,3-dialkyl electrophiles was performed under mild conditions that allowed traditionally reactive functional groups to be included. Mechanistic inspection and control experiments revealed the importance of dual catalysis and that the reaction proceeds via a stepwise oxidative addition followed by an intramolecular SN2 reaction.
Topics & Concepts
ElectrophileChemistryIntramolecular forceCatalysisAlkylSN2 reactionMedicinal chemistryCombinatorial chemistryNickelPhotochemistryStereochemistryOrganic chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCyclopropane Reaction Mechanisms