A stereoconvergent nickel-catalyzed cross-electrophile coupling to afford mono- and di-substituted cyclopropanes will be presented. This intramolecular reaction utilizes 1,3-diol derivates in order to forge previously hard-to-access cyclopropane products, including enantioenriched variants without vestigial directing groups. The mechanism of this reaction will be discussed. Finally, a stereoselective nickel catalyzed cross-electrophile coupling between benzylic ethers and difluoromethyl groups to afford <i>cis-</i>fluorocyclopropanes will be shown. This reaction is unique in that it activates fluoride as a leaving group in order to obtain hard-to-access and medicinally relevant fluorocyclopropanes.

Nickel catalyzed cross electrophile coupling reactions to synthesize enantiopure and fluorinated cyclopropanes

ACS Fall 2021

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