108770-97-4Relevant academic research and scientific papers
Diaryl sulfoxides from aryl benzyl sulfoxides: A single palladium-catalyzed triple relay process
Jia, Tiezheng,Bellomo, Ana,Montel, Sonia,Zhang, Mengnan,El Baina, Kawtar,Zheng, Bing,Walsh, Patrick J.
, p. 260 - 264 (2014)
A novel approach to produce diaryl sulfoxides from aryl benzyl sulfoxides is reported. Optimization of the reaction conditions was performed using high-throughput experimentation techniques. The [Pd(dba)2]/NiXantPhos catalyst system successfully promotes a triple relay process involving sulfoxide α-arylation, C-S bond cleavage, and C-S bond formation. The byproduct benzophenone is formed by an additional palladium-catalyzed process. It is noteworthy that palladium-catalyzed benzylative C-S bond cleavage of sulfoxides is unprecedented. A wide range of aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides with various (hetero)aryl bromides were employed in the triple relay process in good to excellent yields (85-99 %). Moreover, aryl methyl sulfoxides, dibenzyl sulfoxides, and dimethylsulfoxide could be utilized to generate diaryl sulfoxides involving multiple catalytic cycles by a single catalyst. Three for one: The [Pd(dba)2]/NiXantPhos (dba=dibenzylideneacetone) catalyst system successfully promotes a triple relay process involving sulfoxide α-arylation, C-S bond cleavage, and C-S bond formation to give diaryl sulfoxides (see picture). Aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides reacted with various (hetero)aryl bromides. Copyright
2-pyridyl sulfoxide: A versatile and removable directing group for the PdII-catalyzed direct C-H olefination of arenes
Garcia-Rubia, Alfonso,Fernandez-Ibanez, M. Ungeles,Gomez Arrayas, Ramon,Carretero, Juan Carlos
, p. 3567 - 3570 (2011/05/12)
Removable and versatile: The 2-pyridylsulfinyl group has proved to be an efficient directing group in the PdII-catalyzed aryl ortho C-H olefination. This catalyst system enables the sequential double olefination to give asymmetrically di-ortho-functionalized arenes. The sulfinyl directing group can be easily cleaved, providing access to 1,3-disubstituted arenes, or transformed into a thiol group.
