Nickel-Catalyzed Negishi Cross-Coupling of Alkyl Halides, Including Unactivated Tertiary Halides, with a Boron-Stabilized Organozinc Reagent
Panchi Guo, Hao Jin, Jinhui Han, Liang Xu, Pengfei Li, Miao Zhan
Abstract
Nickel-catalyzed cross-coupling of unactivated tertiary alkyl electrophiles with alkylmetal reagents is still a challenge. We report herein a nickel-catalyzed Negishi cross-coupling of alkyl halides, including unactivated tertiary halides, with boron-stabilized organozinc reagent BpinCH 2 ZnI, yielding versatile organoboron products with high functional-group tolerance. Importantly, the Bpin group was found to be indispensable for accessing the quaternary carbon center. The synthetic practicability of the prepared quaternary organoboronates was demonstrated by their conversion to other useful compounds.
Topics & Concepts
Negishi couplingHalideAlkylChemistryReagentNickelCatalysisElectrophileBoronQuaternary carbonFunctional groupOrganic chemistryMedicinal chemistryCombinatorial chemistryEnantioselective synthesisPolymerCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods