37488-68-9Relevant academic research and scientific papers
Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
Kanyiva, Kyalo Stephen,Shibata, Takanori,Uchida, Kanako
, p. 1377 - 1384 (2021/06/06)
We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.
Micellar catalysis using a photochromic surfactant: Application to the pd-catalyzed tsuji-trost reaction in water
Billamboz, Muriel,Mangin, Floriane,Drillaud, Nicolas,Chevrin-Villette, Carole,Banaszak-Leonard, Estelle,Len, Christophe
, p. 493 - 500 (2014/04/03)
The first example of a Pd-catalyzed Tsuji-Trost reaction, applied in a photochromic micellar media under conventional heating and microwave irradiation, is reported. The surfactant activity and recycling ability were investigated and compared with those of a few commercially available surfactants. The synthetic photochromic surfactant proved to be efficient, recyclable, and versatile for Pdcatalyzed coupling reactions.
Iron (III) chloride-catalyzed direct sulfonylation of alcohols with sodium arenesulfinates
Reddy, M. Amarnath,Reddy, P. Surendra,Sreedhar
supporting information; experimental part, p. 1861 - 1869 (2010/10/21)
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
Practical Pd/C-mediated allylic substitution in water
Felpin, Francois-Xavier,Landais, Yannick
, p. 6441 - 6446 (2007/10/03)
Pd/C-mediated allylic substitution in water is described as an interesting alternative to classical homogeneous conditions. The reaction applied to allylic acetates showed a wide range of compatibility with various nitrogen, sulfur, oxygen, and carbon nucleophiles. Notably, the method features inexpensive reagents and a nontoxic solvent. Moreover, measurement of the palladium content in water by ICP-MS shows low palladium contamination (4 ppm) of the solvent, rendering this method safer for the environment compared to homogeneous conditions. The first asymmetric example of Pd/C-mediated allylic substitution is also disclosed.
Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media
Saikia, Promod,Laskar, Dhrubojyoti D.,Prajapati, Dipak,Sandhu, Jagir S.
, p. 512 - 513 (2007/10/03)
A simple and inexpensive procedure for the coupling of sulfonyl chlorides and alkyl halides with aluminum chloride-iron system at ambient temperature in high yield is achieved in aqueous media.
Bi or Cd-induced coupling of sulfonyl chlorides with allylic halides. A simple synthesis of allylic sulfones
Baruah, Mukulesh,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
, p. 1083 - 1084 (2007/10/03)
The bismuth or cadmium-catalyzed coupling reaction between aryl and alkyl sulfonyl chlorides and allylic halides proceeds smoothly to provide excellent yields of allylic sulfones at ambient temperature.
The Preparation of Pyrrole-2-carboxylates from Vinyl Sulfones
Arnold, Dennis P.,Burgess-Dean, Leon,Hubbard, Jason,Rahman, M. Abdur
, p. 969 - 974 (2007/10/02)
The reaction of the anion of ethyl isocyanoacetate with suitably substituted vinyl p-tolyl sulfones gives fair to good yields of pyrrole-2-carboxylates substituted in the 3-, 4- or 3- and 4-positions.From the reaction of 1-phenyl-1-tolylsulfonylethene with ethyl isocyanoacetate, two diastereoisomers of ethyl 4,6-diphenyl-4,6-bis(p-tolylsulfonyl)-3,4,5,6-tetrahydro-2H-azepine-2-carboxylate (4) were also isolated.
SINGLE-STEP PREPARATION OF ALLYLIC SULFIDES HAVING 1-PHENYLTETRAZOLE-5-THIO GROUP FROM ALLYLIC ALCOHOLS USING S,S'-BIS(1-PHENYL-1H-TETRAZOL-5-YL) DITHIOCARBONATE AND REACTIONS INVOLVING THE ALLYLIC SULFIDES
Takeda, Kazuyoshi,Tsuboyama, Kanoko,Torii, Katsumi,Murata, Maki,Ogura, Haruo
, p. 4105 - 4108 (2007/10/02)
The reaction of allylic alcohols and S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (1) gave allylic sulfides having 1-phenyltetrazole-5-thio group in a single step.Furthermore, these allylic sulfides could be applied to carbon-carbon bond and carbon-sulfur bond formations by using Grignard reagents or carbanions in the presence of catalytic amount of copper(I) bromide or palladium (0), respectively.
Rearrangement of Some Allylic Sulphinate Esters to Allylic Sulphones. Ion-pair and Sigmatropic Shift Mechanisms
Knight, Derek J.,Whitham, Gordon H.,Williams, Jonathan G.
, p. 2149 - 2152 (2007/10/02)
The mechanism of rearrangement of a number of allylic sulphinate esters to the corresponding allylic sulphones on heating in formamide has been investigated as a function of substrate structure.Simple systems such as crotyl and α-methylallyl-sulphinate ap
