- Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
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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.
- Kanyiva, Kyalo Stephen,Shibata, Takanori,Uchida, Kanako
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p. 1377 - 1384
(2021/06/06)
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- Micellar catalysis using a photochromic surfactant: Application to the pd-catalyzed tsuji-trost reaction in water
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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.
- Billamboz, Muriel,Mangin, Floriane,Drillaud, Nicolas,Chevrin-Villette, Carole,Banaszak-Leonard, Estelle,Len, Christophe
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p. 493 - 500
(2014/04/03)
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- Iron (III) chloride-catalyzed direct sulfonylation of alcohols with sodium arenesulfinates
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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
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supporting information; experimental part
p. 1861 - 1869
(2010/10/21)
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- Practical Pd/C-mediated allylic substitution in water
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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.
- Felpin, Francois-Xavier,Landais, Yannick
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p. 6441 - 6446
(2007/10/03)
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- Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media
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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.
- Saikia, Promod,Laskar, Dhrubojyoti D.,Prajapati, Dipak,Sandhu, Jagir S.
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p. 512 - 513
(2007/10/03)
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- Bi or Cd-induced coupling of sulfonyl chlorides with allylic halides. A simple synthesis of allylic sulfones
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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.
- Baruah, Mukulesh,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
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p. 1083 - 1084
(2007/10/03)
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- The Preparation of Pyrrole-2-carboxylates from Vinyl Sulfones
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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.
- Arnold, Dennis P.,Burgess-Dean, Leon,Hubbard, Jason,Rahman, M. Abdur
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p. 969 - 974
(2007/10/02)
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- 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
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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.
- Takeda, Kazuyoshi,Tsuboyama, Kanoko,Torii, Katsumi,Murata, Maki,Ogura, Haruo
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p. 4105 - 4108
(2007/10/02)
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- Rearrangement of Some Allylic Sulphinate Esters to Allylic Sulphones. Ion-pair and Sigmatropic Shift Mechanisms
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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
- Knight, Derek J.,Whitham, Gordon H.,Williams, Jonathan G.
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p. 2149 - 2152
(2007/10/02)
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- Preparation of some Allylic Sulphones; Base-catalysed Isomerisation and Deuteriation of Cyclohex-2-enyl p-Tolyl Sulphones
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A summary of the methods used in the preparation of a range of allylic sulphones is given.In the case of the conformationally biased sulphones (5) and (6) stereospecific preparation from the cis- and trans-5-t-butylcyclohex-2-en-1-ols was achieved by rear
- Knight, Derek J.,Lin, Peter,Russell, Simon T.,Whitham, Gordon H.
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p. 2701 - 2706
(2007/10/02)
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