Catalytic Rearrangement of Aldoximes to Primary Amides in Environmentally Friendly Media under Thermal and Microwave Heating: Another Application of the Bis(allyl)-Ruthenium(IV) Dimer [{RuCl(μ-Cl)(η3:η3-C10H16)}2]

Abstract

The rearrangement of aldoximes to primary amides has been studied using the commercially available bis(allyl)-ruthenium(IV) complex [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (1; C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) as a catalyst under thermal and microwave heating. The reactions proceeded cleanly in a mixture of water/glycerol (1:1) at 120-150°C, without the assistance of any cocatalyst, affording the desired amides in moderate to high yields and short times. The process was operative with aromatic, heteroaromatic, aliphatic, and α,β-unsaturated aldoximes and tolerated the presence of several functional groups in the substrates. In addition, the recyclability of catalyst 1 (up to six consecutive runs) could be demonstrated.