Aromatic ortho-benzylation reveals an unexpected reductant.
The discovery of a novel arylpalladium(II) reduction enables the synthesis of diarylmethanes via reductive benzylation. Benzyl chlorides were found to be the major source of hydride, acting as an alkylating agent and an aprotic surrogate for benzyl alcohol. This represents the first example of an arylpalladium(II) reduction mediated by a benzyl halide.
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Andrew
A
Martins
Mark
M
Lautens
D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D019163:Reducing Agents / Q000737:chemistry*
D001593:Benzyl Compounds; D007454:Iodides; D019163:Reducing Agents; C021292:benzyl chloride