Simplifying Nickel(0) Catalysis: An Air-stable, COD-free Nickel Precatalyst for the Internally-selective Benzylation of Terminal Alkenes
Author(s)
Jamison, Timothy F.; Standley, Eric Alan
DownloadEAS TFJ Manuscript (Revised).pdf (1.048Mb)
OPEN_ACCESS_POLICY
Open Access Policy
Creative Commons Attribution-Noncommercial-Share Alike
Alternative title
Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes
Terms of use
Metadata
Show full item recordAbstract
The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy[subscript 2]Ph)[subscript 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.
Date issued
2013-01Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Standley, Eric A., and Timothy F. Jamison. “Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes.” Journal of the American Chemical Society 135, no. 4 (January 30, 2013): 1585-1592.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126