Cross-couplings using tertiary alkyl halides as electrophilic reaction partners are relatively elusive in the literature. Such processes are regarded to be challenging due to the steric demand of tertiary alkyl halides, as well as their propensity to decompose through elimination pathways during the course of the reaction. We report the first Suzuki-Miyaura cross-couplings of tertiary alkyl halides, specifically, reactions of unactivated alkyl bromides with aryl-(9-BBN) reagents. The development of the conditions and scope of this methodology will be presented. 

Nickel-catalyzed Suzuki–Miyaura cross-couplings of unactivated tertiary alkyl bromides with aryl-(9-BBN) reagents

244th National Meeting (2012)

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