The Carbonylation of Phenylcopper Tri-n -Butylphosphine Complex [PhCu.P(n-Butyl)3] Produces the Symmetrical Ketone Benzophenone

Abstract

The Carbonylation of Phenylcopper Tri-n -Butylphosphine Complex [PhCu.P(n-Butyl)3] Produces the Symmetrical Ketone Benzophenone Jennifer A. Ebert, Greg W. Ebert Abstract In 1972 Jeffrey Schwartz of Massachusetts Institute of Technology published a seminal paper on the reaction of carbon monoxide with alkylcopper complexes to form symmetrical ketones (Schwartz, 1972). This was one of the earliest examples of the carbonylation of an organocopper reagent and gave a tantalizing glimpse into the possibility of forming copper acyl anion complexes. While that work examines alkylcopper reagents in some detail, no mention is made concerning the study of aromatic copper reagents. We were interested in exploring whether or not a similar approach could be used to carbonylate and convert arylcopper reagents into symmetrical aryl ketones thereby opening up this reaction to aromatic organocopper compounds. We now wish to report the successful carbonylation of phenylcopper tri-n-butylphosphine complex [PhCu.P(n-butyl)3] to produce the symmetrical ketone benzophenone: PhCu.P(n-butyl)3 + CO → Ph-C(O)-Ph Full Text: PDF DOI: 10.15640/jcb.v7n2a2