Green and Efficient Synthesis of Sulfonamides Catalyzed by Nano-Ru/Fe3O4

• DOI: 10.1021/ja807681v
• Publication Date: 2009-01-21T15:15:02Z
• Authors: Feng Shi; Man Kin Tse; Shaolin Zhou; Marga-Martina Pohl; Jörg Radnik; Sandra Hübner; Klaus Jähnisch; Angelika Brückner; Matthias Beller
• Keywords: Sulfonamide; Benzyl alcohol

The environmentally benign synthesis of carbon−nitrogen bonds continues to be an active and challenging field chemical research. Here, a novel, method for the direct coupling sulfonamides alcohols is described. Despite importance sulfonamide derivatives as intermediates in drug synthesis, till now such transformations are rarely known. For first time domino dehydrogenation-condensation-hydrogenation sequence has been realized presence nanostructured catalyst. magnetic property catalyst system allows convenient isolation product efficient recycling A variety reactions benzylic including various heterocycles were successfully realized, often with >80% isolated yield. Advantageously, only one equivalent primary alcohol consumed process. Mechanistic investigations competitive benzyl d7-benzyl p-toluenesulfonamide revealed kinetic isotope effect (kH/kD) 2.86 (±0.109) dehydrogenation 0.74 (±0.021) hydrogenation N-benzylidene-p-toluenesulfonamide intermediate, which suggests rate determining step.