A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

• Erwan Le Gall,
• Antoine Pignon and
• Thierry Martens

Beilstein J. Org. Chem. 2011, 7, 997–1002, doi:10.3762/bjoc.7.112

• to iminium ions. Consequently, we report herein the use of primary amines in a sequential one-pot process, based on the preliminary activation of an aldimine with an acyl chloride or a chloroformate, and the subsequent trapping of the resulting acyliminium ion with an aromatic organozinc reagent, to

• -amine, taken as a model aldimine, which was preformed and purified prior to use. This compound was subjected to consecutive reactions with acetyl chloride and phenylzinc bromide, furnishing the corresponding diarylmethylamide in good yield (80%). However, as supplementary experiments indicated that the

• chloride as an activator, whose reaction with the model aldimine and phenylzinc bromide did not afford the expected compound. On the other hand, a preliminary experiment indicated that trifluoracetic anhydride was a very reliable activator of the imine towards phenylzinc bromide addition. These results