24362-84-3Relevant articles and documents
Tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts
Gelat, Fabien,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Perrio, Stéphane
supporting information, p. 2011 - 2016 (2015/06/23)
The present report describes an efficient and clean generation of sulfenate salts (R1SO-) by pyrolysis of readily available tert-butyl sulfoxides to give sulfenic acids (R1SOH) and traceless isobutene, followed by hydrogen abstraction with a weak inorganic base (K3PO4). The relevance of this process was exemplified through an in situ palladium-catalyzed cross-coupling reaction with aryl halides/triflates leading to aryl sulfoxides. The operationally simple C-S bond-forming protocol developed uses Pd(dba)2 as catalyst and Xantphos as ligand in toluene or a toluene/H2O mixture. Further extensions include the use of di-tert-butyl sulfoxide as an equivalent for sulfur monoxide dianion (SO2-) and the development of diastereoselective versions in the [2.2]paracyclophane and biaryl series.
Facile preparation of aryl sulfides using palladium catalysis under mild conditions
Okauchi, Tatsuo,Kuramoto, Kouji,Kitamura, Mitsuru
supporting information; experimental part, p. 2891 - 2894 (2011/02/28)
A convenient method for C-S cross-coupling of aryl bromides with various thiols has been developed that involves the use of a 1,1′- bis(diphenylphosphino)ferrocene (DPPF)-ligated palladium complex with N,N-diisopropylethylamine (DIPEA) as the base. This coupling is tolerant of a wide range of functional groups, including hydroxy, amino, cyano, nitro, formyl, and carboxyl groups. Georg Thieme Verlag Stuttgart - New York.
Oxidation of Alkylthio Substituted Tricarbonyl(η6-arene)chromium(0) Complexes to Alkylsulfinyl Substituted Tricarbonyl(η6-arene)chromium(0) Complexes
Perez-Encabo, Alfonso,Perrio, Stephane,Slawin, Alexandra M. Z.,Thomas, Susan E.,Wierzchleyski, Adam T.,Williams, David J.
, p. 629 - 642 (2007/10/02)
Dimethyldioxirane efficiently oxidises tricarbonylchromium(0) complexes of alkylthio substituted arenes to tricarbonylchromium(0) complexes of alkylsulfinyl substituted arenes.The diastereoselectivity of oxidation of ortho substituted complexes, which was determined by inter alia X-ray crystal structure analyses of tricarbonyl6-1-methoxy-2-(methylsulfinyl)benzene>-chromium(0) 20x, 6-1-(tert-butylsulfinyl)-2-methoxybenzene>tricarbonylchromium(0) 23x and tricarbonyl6-1-(ethylsulfinyl)-2-methoxybenzene)chromium(0) 21y, is dependent on the alkylthio substituent and is reversed when this substituent is changed from methylthio to tert-butylthio.