N2 extrusion and CO insertion: a novel palladium-catalyzed carbonylative transformation of aryltriazenes

Org Lett. 2015 Apr 17;17(8):1910-3. doi: 10.1021/acs.orglett.5b00603. Epub 2015 Mar 31.

Abstract

A novel procedure for the replacement of N2 with CO of aryltriazenes has been developed. Aryltriazenes were converted to the corresponding arylamides catalyzed by 1 mol % of PdCl2/P(o-Tol)3 under CO pressure. In this process, aryldiazonium salts were generated in the presence of 40 mol % of MeSO3H. Nitrogen was released from the substrates and CO formally inserted. Aryl bromides, iodides, alkynes, and free hydroxyl groups can be tolerated in this transformation.