24362-84-3Relevant academic research and scientific papers
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.
Carbon-sulfur bond formation of challenging substrates at low temperature by using Pd-PEPPSI-IPent
Sayah, Mahmoud,Organ, Michael G.
supporting information; experimental part, p. 11719 - 11722 (2011/11/29)
Aryl thiols made cool and quick: The coupling of alkyl, aryl, and silyl thiols to hindered, deactivated aryl bromides and chlorides has been achieved under the most mild temperatures yet reported (i.e., room temperature to 40°C). The bulk afforded by the di-2,6-(3-propylphenyl)imidazolium-derived Pd-PEPPSI-IPent catalyst is believed to actively promote the critical reductive elimination step of the catalytic cycle, thereby eliminating the formation of poisonous off-cycle dimeric resting states that have plagued Pd-catalyzed sulfination reactions.
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.
Zinc-mediated palladium-catalyzed formation of carbon-sulfur bonds
Eichman, Chad C.,Stambuli, James P.
supporting information; experimental part, p. 4005 - 4008 (2009/10/02)
(Chemical Equation Presented) A catalytic amount of zinc chloride in combination with a palladium catalyst ligated by a monodentate phosphine allows the coupling of aryl and alkyl thiols with aryl bromides in high yields. The addition of zinc chloride to a palladium catalyst system that reportedly failed to promote sulfide formation allows this once ineffective catalyst system to provide the sulfide product in good yield. This paper describes a high-yielding and general monodentate phosphine-ligated palladium catalyst for biaryl and alkyl aryl sulfide formation.
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.
ortho-Substituted Unsymmetrical Biaryls from Aryl tert-Butyl Sulfones
Clayden, Jonathan,Julia, Marc
, p. 1682 - 1683 (2007/10/02)
Nickel-catalysed coupling of arylmagnesium halides with aryl tert-butyl sulfones, and in particular with those bearing ortho-substituents introduced by ortholithiation, gives ortho-substituted unsymmetrical biaryls.
