33521-88-9Relevant articles and documents
Synthesis of alkenyl sulfides through the iron-catalyzed cross-coupling reaction of vinyl halides with thiols
Lin, Yun-Yung,Wang, Yu-Jen,Lin, Che-Hung,Cheng, Jun-Hao,Lee, Chin-Fa
experimental part, p. 6100 - 6106 (2012/10/08)
We report here the iron-catalyzed cross-coupling reaction of alkyl vinyl halides with thiols. While many works are devoted to the coupling of thiols with alkyl vinyl iodides, interestingly, the known S-vinylation of vinyl bromides and chlorides is limited
Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides
Sacasa, Pablo R.,Zayas, Jessica,Wnuk, Stanislaw F.
experimental part, p. 5424 - 5427 (2009/12/06)
Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.
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.
