Green and Efficient Synthesis of Sulfonamides Catalyzed by Nano-Ru/Fe3O4
Sulfonamide
Benzyl alcohol
DOI:
10.1021/ja807681v
Publication Date:
2009-01-21T15:15:02Z
AUTHORS (9)
ABSTRACT
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.
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