The activation of unstrained, neutral C–N bonds towards cross-electrophile coupling is enabled through nickel catalysis. A nickel-catalyzed domino cross-electrophile coupling reaction of alkynyl substituted piperidines to form vinylcyclopropanes with a tetrasubstituted alkene will be discussed. This domino reaction is a rare example that involves a cross-electrophile coupling as a discrete step. The scope of the reaction has been expanded to include substituents with both electron-donating and electron-withdrawing groups. The mechanism of this domino reaction has also been investigated utilizing a cross-over experiment. The domino reaction products have been derivatized to illustrate synthetic utility. A method for the synthesis of organohalides will also be discussed, including the substrate scope of the reaction.

Development of a nickel-catalyzed domino cross-electrophile coupling dicarbofunctionalization reaction of alkynyl <i>N-</i>tosylpiperidines and a synthesis of organohalides

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Development of a nickel-catalyzed domino cross-electrophile coupling dicarbofunctionalization reaction of alkynyl N-tosylpiperidines and a synthesis of organohalides