title: Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.
abstract: The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy(2)Ph)(2)Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.
authors: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors: Eric A
authors: EA
authors: Standley
authors: Timothy F
authors: TF
authors: Jamison
mesh_terms: D000388:Air; D000475:Alkenes / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D000081248:Allylbenzene Derivatives
chemical_list: D000475:Alkenes; D000498:Allyl Compounds; D001555:Benzene Derivatives; D009532:Nickel; D009942:Organometallic Compounds; C102347:allylbenzene; D000081248:Allylbenzene Derivatives