An attempted nickel-mediated macrocyclization of aryl chlorides yielded an unexpected product in which an alkyne is transformed into two quaternary carbons by four-fold arylation. Of the potential products that could form, the isolated, predominant product has an unprecedented, chiral structure. X-ray crystallographic analysis confirms the molecular structure of the product, and enantiomers are separable by chiral HPLC. Synthesis, structural properties, and a mechanistic proposal for the reaction will be presented.

Unexpected four-fold intramolecular arylation of an alkyne

ACS Spring 2022

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