Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF3 · Et2O: Facile access to sulfinates and sulfones
An efficient BF3 · Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C–O and C–S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that provide highly stabilized carbocation in the reaction medium afforded sulfones as sole products. This study was aimed at understanding the regioselectivity of ambidentate sulfinate ion and to elucidate the interpretation of sulfinate/sulfone scaffolds.
Pogaku, Naresh,Krishna, Palakodety Radha,Prapurna, Y. Lakshmi
supporting information
p. 1239 - 1249
(2017/07/06)
Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate
A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.
Nambo, Masakazu,Ariki, Zachary T.,Canseco-Gonzalez, Daniel,Beattie, D. Dawson,Crudden, Cathleen M.
supporting information
p. 2339 - 2342
(2016/06/09)
Direct sulfonylation of Baylis-Hillman alcohols and diarylmethanols with TosMIC in ionic liquid-[Hmim]HSO4: An unexpected reaction
A Bronsted acidic ionic liquid-[Hmim]HSO4 promoted unexpected reaction of Baylis-Hillman alcohols and diarylmethanols with p-toluenesulfonylmethyl isocyanide (TosMIC) affording the corresponding sulfone derivatives instead of N-tosylmethyl amid
Garima,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
experimental part
p. 4622 - 4626
(2011/09/21)
Iron (III) chloride-catalyzed direct sulfonylation of alcohols with sodium arenesulfinates
A new protocol for the direct sulfonylation of benzylic, allylic and homoallylic alcohols with sodium arenesulfinates is described by using iron (III) chloride as a catalyst and chlorotrimethylsilane as an additive. This method requires no preactivation o
Reddy, M. Amarnath,Reddy, P. Surendra,Sreedhar
supporting information; experimental part
p. 1861 - 1869
(2010/10/21)
Palladium-catalyzed benzylic direct arylation of benzyl sulfones with aryl halides
An effective palladium catalyst system for the direct arylation of benzyl sulfones with aryl halides has been developed. The catalytic reaction provides a facile route to diarylmethyl sulfones. The products can be transformed further via desulfonylative functionalization mediated by aluminum compounds.
Niwa, Takashi,Yorimitsu, Hideki,Oshima, Koichiro
experimental part
p. 1971 - 1976
(2009/08/07)
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