Nickel-catalyzed cross-couplings of unactivated alkyl halides and pseudohalides with organometallic compounds

Until recently, there had been a widespread perception that unactivated, beta-hydrogen-containing alkyl halides/pseudohalides are not suitable partners for nickel-catalyzed coupling reactions. During the past several years, a number of reports have dispelled this misconception by demonstrating that a diverse array of electrophiles and organometallic reagents can in fact be efficiently cross-coupled. 1 Introduction 2 Negisbi Couplings 2.1 Couplings of Primary Alkyl Halides 2.2 Couplings of Secondary Alkyl Halides 3 Suzuki Couplings of Primary and Secondary Alkyl Halides with Unsaturated Boronic Acids 4 Hiyama Couplings of Primary and Secondary Alkyl Halides with Trifluoroarylsilanes 5 Kumada Couplings of Primary Alkyl Halides and Tosylates with Grignard Reagents 6 Conclusions and Future Outlook