- Indium-catalyzed reductive three-component coupling reaction of aliphatic/aromatic carboxylic acids with t-butyl mercaptan leading to unsymmetrical dialkyl sulfides
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An InI3–TMDS (1,1,3,3-tetramethyldisiloxane) reducing system efficiently catalyzed a sequential three-component coupling of aliphatic carboxylic acids, aromatic carboxylic acids, and t-butyl mercaptan (t-butylthiol), to produce unsymmetrical dialkyl sulfides. With this reducing system, t-butyl mercaptan became a new source of sulfidation via an alkyl t-butyl sulfide that functioned as the reaction intermediate.
- Sakai, Norio,Yoshimoto, Shunsuke,Miyazaki, Takahiro,Ogiwara, Yohei
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supporting information
p. 3117 - 3120
(2016/07/06)
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- One-pot Metal-free Synthesis of Benzyl Alkyl Sulfides
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The synthesis of sulfides is important in various fields. This paper reports an efficient, odorless, and viable protocol for the base-mediated synthesis of benzyl alkyl sulfides using thiourea. The reactions were carried out under transition-metal-free co
- Lu, Xiaogang,Wang, Hongmei,Gao, Runli,Pei, Chengxin
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- A highly efficient heterogeneous rhodium(I)-catalyzed C-S coupling reaction of thiols with polychloroalkanes or alkyl halides under mild conditions
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Heterogeneous C-S coupling reaction of thiols with polychloroalkanes or alkyl halides was achieved at 30 or 80 °C in the presence of 5 mol% of an MCM-41-immobilized bidentate phosphine rhodium complex (MCM-41-2P-RhCl(PPh3)) and triethylamine, yielding a variety of formaldehyde dithioacetals, ethylenedithioethers and unsymmetric thioethers in good to excellent yields. This heterogeneous rhodium catalyst can be easily recovered and recycled by simple filtration of the reaction solution and used for at least 10 consecutive trials without significant loss of activity.
- Xia, Jianhui,Yao, Ruiya,Cai, Mingzhong
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p. 221 - 225
(2015/03/30)
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- Silica-promoted facile synthesis of thioesters and thioethers: A highly efficient, reusable and environmentally safe solid support
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An efficient, mild and rapid procedure for the acylation and alkylation of aromatic and aliphatic thiols mediated on a silica gel surface at room temperature is described. The protocol allows the protection of thiols under neutral heterogeneous conditions without requiring any bases or Lewis acids, and the silica gel used as the promoter can be recycled for several runs without any loss of activity.
- Basu, Basudeb,Paul, Susmita,Nanda, Ashis K.
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experimental part
p. 767 - 771
(2010/09/05)
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- ZrCl4 dispersed on dry silica gel provides a useful reagent for S-alkylation of thiols with alcohols under solvent-free conditions
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ZrCl4 which is commercially available and not a costly compound, is a relatively safe chemical [LD50 [ZrCl4, oral rat] = 1688 mg Kg]. In this report we describe the use of ZrCl4 dispersed on dry silica gel as an efficient reagent for the efficient preparation of thioethers from thiols with alcohols under solvent-free conditions.
- Firouzabadi, Habib,Iranpoor, Nasser,Jafarpour, Maasoumeh
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- CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers
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Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.
- Shah, Syed T. A.,Khan, Khalid M.,Hussain, Hidayat,Hayat, Safdar,Voelter, Wolfgang
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p. 1583 - 1589
(2007/10/03)
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- An alternative approach towards the syntheses of thioethers and thioesters using CsF-Celite in acetonitrile
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It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride-Celite. In this manner, compounds like ethanethiol, 1-pentanethiol, thiophenol, 4-methoxythiophenol, 4-nitrothiophenol, and 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, and 2-mercapto-2-thiazoline can be successfully alkylated, acylated, benzylated or benzoylated. This procedure is convenient, efficient and practical for the preparation of thioethers and thioesters.
- Shah, Syed Tasadaque Ali,Khan, Khalid Mohammed,Martinez Heinrich, Angelica,Voelter, Wolfgang
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p. 8281 - 8283
(2007/10/03)
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- Biotransformation of organic sulfides - VIII. A predictive model for sulfoxidation by Helminthosporium species NRRL 4671
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The fungus Helminthosporium species NRRL 4671 converts a wide range of prochiral sulfides to the corresponding chiral sulfoxides, the majority of which have (S) configuration at sulfur. The formation of a series of chiral cyclopentyl alkyl, cyclohexyl alkyl, benzyl alkyl, and methyl alkyl sulfoxides by biotransformation of the corresponding sulfides using Helminthosporium species is described. The analysis of over 90 such biotransformations has resulted in the development of a model based on restrictive-space descriptors that has been used to rationalize these reactions, and that is proposed as a predictor of the outcome of Helminthosporium-catalyzed sulfoxidations.
- Holland, Herbert L.,Brown, Frances M.,Lakshmaiah, Gingipalli,Larsen, Brett G.,Patel, Manish
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p. 683 - 697
(2007/10/03)
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- An Odorless Preparative Method of Sulfides and Thiocarboxylic S-Esters Using 3-(Alkylthio)-1,2-benzisothiazole 1,1-Dioxide
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It was found that sodium salt of 1,2-benzisothiazole-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide (3).Treatment of 3 with piperidine produces the corresponding alkanethiol in situ quantitatively and subsequent treatment with various electrophiles gives the corresponding sulfides and thiocarboxylic S-esters in good yields.
- Yamada, Hiroyuki,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
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p. 949 - 950
(2007/10/02)
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