141726-98-9Relevant academic research and scientific papers
Hole transfer promoted hydrogenation: One-electron oxidation as a strategy for selective reduction of π-bonds
Mirafzal, Gholam A.,Liu, Jianping,Bauld, Nathan L.
, p. 6072 - 6077 (2007/10/02)
One-electron oxidation is developed as a strategy for selective and efficient reduction of relatively ionizable functionalities, including conjugated dienes, styrenes, vinyl sulfides, aromatics, and even strained σ-bonds. Reduction is highly sensitive to substrate ionizability and permits selective reduction of the more ionizable function in a difunctional context. Ionization of the substrates to cation radicals is effected via the mild hole transfer agent tris(4-bromophenyl)aminium hexachloroantimonate, and subsequent reduction of the cation radicals is accomplished by tributyltin hydride. The new reduction conditions provide a novel route for generating free radicals which may prove useful in the field of radical cyclizations. This is especially attractive in the case of phenyl vinyl sulfides since the phenylthio group, which remains intact subsequent to cyclization, provides versatile functionality for further synthetic operations.
