title: Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.
abstract: Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more commonly observed 1,2-disubstituted olefins with very high selectivity.
authors: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors: Ryosuke
authors: R
authors: Matsubara
authors: Alicia C
authors: AC
authors: Gutierrez
authors: Timothy F
authors: TF
authors: Jamison
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism; D000081248:Allylbenzene Derivatives
chemical_list: D000475:Alkenes; D000498:Allyl Compounds; D001555:Benzene Derivatives; D001593:Benzyl Compounds; D009532:Nickel; C102347:allylbenzene; D000081248:Allylbenzene Derivatives; C021292:benzyl chloride