Simplifying Nickel(0) Catalysis: An Air-stable, COD-free Nickel Precatalyst for the Internally-selective Benzylation of Terminal Alkenes
Name
EAS TFJ Manuscript (Revised).pdf
Size
1.05 MB
Format
Adobe PDF
Checksum (MD5)
d16091393357a70086f7e66a8694b03e
Author(s)
Jamison, Timothy F.
Standley, Eric Alan
Alternative Title
Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes
Date Issued
January 2013
Journal
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
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike 3.0
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DOI of Published Version
https://doi.org/10.1021/ja3116718
