Mechanical Activation of Zero-Valent Metal Reductants for Nickel-Catalyzed Cross-Electrophile Coupling
Andrew C. Jones, Matthew T. J. Williams, Louis C. Morrill, Duncan L. Browne
Abstract
The cross-electrophile coupling of either twisted-amides or heteroaryl halides with alkyl halides, enabled by ball-milling, is herein described. The operationally simple nickel-catalyzed process has no requirement for inert atmosphere or dry solvents and delivers the corresponding acylated or heteroarylated products across a broad range of substrates. Key to negating the necessity of inert reaction conditions is the mechanical activation of the raw metal terminal reductant: manganese in the case of twisted amides and zinc for heteroaryl halides.
Topics & Concepts
HalideElectrophileNickelCatalysisChemistryAlkylMetalInert gasManganeseZincInertTransition metalCoupling reactionInorganic chemistryOrganic chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCoordination Chemistry and Organometallics