- A Simmple Preparation of Aromatic or Heteroaromatic Sulphides
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A simple preparation of alkyl- or aryl-thioaromatic compounds from primary aromatic and heteroaromatic amines and the appropriate disulphides has been effected using isopentyl nitrite.
- Giam, Choo S.,Kikukawa, Kiyoshi
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- Synthesis of substituted pyridines by the reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under focused microwave irradiation
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The nucleophilic substitution reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under microwave irradiation was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to those conducted under conventional heating processes.
- Cherng, Yie-Jia
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- Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
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We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.
- Delcaillau, Tristan,Boehm, Philip,Morandi, Bill
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supporting information
p. 3723 - 3728
(2021/04/07)
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- t-BuOK-promoted methylthiolation of aryl fluorides with dimethyldisulfide under transition-metal-free and mild conditions
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In the presence of potassium tert-butoxide (t-BuOK), the cross-coupling reaction between aryl fluorides and dimethyldisulfide was developed. A series of aryl methyl sulfides were obtained in moderate to good yields under transition-metal-free and mild conditions.
- Huang, Dayun,Wu, Xiangmei
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- Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water
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An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.
- Wang, Ying-Yu,Wu, Xiang-Mei,Yang, Ming-Hua
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supporting information
(2020/07/20)
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- Cesium carbonate-promoted synthesis of aryl methyl sulfides using: S -methylisothiourea sulfate under transition-metal-free conditions
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In the presence of cesium carbonate, an efficient synthesis of aryl methyl sulfides by the reactions of aryl halides with commercially available S-methylisothiourea sulfate is developed. This odourless and highly crystalline solid can be used as the subst
- Zhang, Caiyang,Zhou, You,Huang, Jintao,Tu, Canhui,Zhou, Xiaoai,Yin, Guodong
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p. 6316 - 6321
(2018/09/10)
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- A convenient method for the synthesis of aryl methyl sulfides via Cu(I)-mediated methylthiolation of haloarenes with DMSO
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An efficient process for the Cu(I)-mediated methylthiolation of haloarenes using simple and readily available DMSO as a convenient and environment friendly source of SMe moiety has been developed. In the presence of CuI and DABCO, a variety of aryl/heteroaryl halides reacted with DMSO to afford corresponding aryl methyl sulfides in good to excellent yields.
- Ghosh, Ketaki,Ranjit, Sadananda,Mal, Dipakranjan
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supporting information
p. 5199 - 5202
(2015/08/19)
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- Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases
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Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright
- Rioz-Martinez, Ana,De Gonzalo, Gonzalo,Pazmino, Daniel E. Torres,Fraaije, Marco W.,Gotor, Vicente
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experimental part
p. 6409 - 6416
(2011/02/24)
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- A general and efficient approach to aryl thiols: Cul-catalyzed coupling of aryl iodides with sulfur and subsequent reduction
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A Cul-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K2CO3 at 90 °C. The coupling mixture is directly treated with NaBH4 or triphenylphosphine to afford aryl thiols in good to
- Jiang, Yongwen,Qin, Yuxia,Xie, Siwei,Zhang, Xiaojing,Dong, Jinhua,Ma, Dawei
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supporting information; scheme or table
p. 5250 - 5253
(2009/12/28)
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- TMSCH2Li and TMSCH2Li-LiDMAE: Efficient reagents for noncryogenic halogen-lithium exchange in bromopyridines
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(Chemical Equation Presented) TMSCH2Li and TMSCH 2Li-LiDMAE have been used efficiently for bromine-lithium exchange in 2-bromo-, 3-bromo-, and 2,5-dibromopyridines under noncryogenic conditions, while low temperatures (-78 to -100°C) are always needed with n-BuLi. The aminoalkoxide LiDMAE induced a remarkable C-2 selectivity with 2,5-dibromopyridines in toluene at 0°C, which was unprecedented at such a temperature. The lithiopyridines were successfully reacted witb electrophiles also under noncryogenic conditions giving the expected adducts in good yields.
- Doudouh, Abdelatif,Woltermann, Christopher,Gros, Philippe C.
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p. 4978 - 4980
(2008/02/07)
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- New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine
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The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by
- Comoy, Corinne,Banaszak, Estelle,Fort, Yves
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p. 6036 - 6041
(2007/10/03)
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- Unusual t-BuLi induced ortholithiation versus halogen-lithium exchange in bromopyridines: Two alternative strategies for functionalization
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The reaction of lithiating agents with various 3-bromopyridines has been investigated. An unprecedented selectivity was observed with t-BuLi, which effected a clean lithiation at C-4. With 3-bromo and 2-chloro-3-bromo pyridines, the ortholithiation-exchange ratio was strongly electrophile and addition order dependent while 2-chloro-5-bromopyridine always gave exclusive C-4 substitution.
- Pierrat, Philippe,Gros, Philippe,Fort, Yves
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p. 2319 - 2322
(2007/10/03)
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- One-Pot Two-Step Synthesis of Aryl Sulfur Compounds by Photoinduced Reactions of Thiourea Anion with Aryl Halides
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(Equation presented) The photoinduced reactions of aryl halides with the thiourea anion afford arene thiolate ions in DMSO. These species without isolation, and by a subsequent aliphatic nucleophilic substitution, S RN1 reaction, oxidation, or protonation, yield aryl methyl sulfides, diaryl sulfides, diaryl disulfides, and aryl thiols with good yields (50-80%). This is a simple and convenient approach which involves the use of the commercially available and inexpensive thiourea in a one-pot two-step process for the synthesis of aromatic sulfur compounds.
- Argueello, Juan E.,Schmidt, Luciana C.,Penenory, Alicia B.
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p. 4133 - 4136
(2007/10/03)
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- Azetidine derivatives, their preparation and pharmaceutical compositions containing them
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Compounds of formula: in which R represents a CR1R2, C═C(R5)SO2R6 or C═C(R7)SO2alk radical, their preparation and the pharmaceutical compositions containing them.
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- New syntheses of substituted pyridines via bromine-magnesium exchange
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Bromine-magnesium exchange using iPrMgCl in THF at room temperature on 2-, 3- and 4-bromopyridines allowed the synthesis of various functionalized pyridines. The methodology was successfully used for the synthesis of 4- azaxanthone. Moreover, single exchange reactions observed on 2,6-, 3,5-, 2,3- and 2,5-dibromopyridines, with complete regioselectivity in the case of 2,3- and 2,5-dibromopyridines, afforded substituted bromopyridines, which were then involved in a second exchange step to provide difunctionalized pyridines. (C) 2000 Elsevier Science Ltd.
- Trécourt, Fran?ois,Breton, Gilles,Bonnet, Véronique,Mongin, Florence,Marsais, Francis,Quéguiner, Guy
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p. 1349 - 1360
(2007/10/03)
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- Pyridylmagnesium chlorides from bromo and dibromopyridines by bromine- magnesium exchange: A convenient access to functionalized pyridines
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Various bromopyridines were converted to the corresponding pyridylmagnesium chlorides at room temperature by treatment with iPrMgCl. The resulting Grignard reagents were quenched by various electrophiles to afford functionalized pyridines. The bromine-magnesium exchange of some dibromopyridines was also studied.
- Trecourt, Francois,Breton, Gilles,Bonnet, Veronique,Mongin, Florence,Marsais, Francis,Queguiner, Guy
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p. 4339 - 4342
(2007/10/03)
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- SYNTHESIS AND BEHAVIOUR OF NADH MODELS BEARING A CHIRAL SULFOXIDE
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Chiral 3-sulfinyl-1,4-dihydropyridine derivatives were synthesized by asymmetric oxidation of the parent 3-pyridine sulfides with Kagan's reagent (Ti(OiPr)4/diethyl tartrate/H2O/tBuOOH = 1/2/1/1).The chemoselective oxidation conditions of the sulfur atom were optimized.One chiral NADH mimic reagent so obtained was used in the reduction of prochiral α,α',α''-trifluoroacetophenone.During this reduction a side reaction occurred i.e. desulfenylation of the reagent.The by-product was identified after trapping with methyl propiolate.This side reaction did not occur in the quinoline series.
- Boussad, N.,Trefouel, T.,Dupas, G.,Bourguignon, J.,Queguiner, G.
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p. 127 - 138
(2007/10/02)
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- CONFORMATIONAL AND PHOTOELECTRON ANALYSIS OF ISOMERS OF THE METHYLCHALCOGENOPYRIDINES
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The He I/He II photoelectron spectra of 2-, 3-, and 4-methylthio- and methylselenyl-pyridine are reported and interpreted in terms of a composite-molecule model based on ab initio calculations.Results from STO-3G* calculations at STO-3G* optimised geometries suggest that, for the 2- and 4-isomers, the planar conformer is more stable than the non-planar conformer, although bands due to the minor conformers are evident in some of the spectra.The He I/He II band ratios are shown to be useful in locating those MOs with significant S or Se p AO contributions, thereby indicating the chalcogene content in the bonding and anti-bonding X-? orbitals.Based on spectral features, He I/He II ratios and in conjunction with ab initio calculations, the preferred sequence for the four lowest ionisation energies for all isomers of the methylchalcogenopyridines is ? - nX N ca. ? X, where X represents the chalcogen atom.
- Dunne, Simon J.,Summers, Lindsay A.,Nagy-Felsobuky, Ellak I. von
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p. 103 - 120
(2007/10/02)
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- Functionalization of Pyridine via Direct Metallation
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The isolation of mixtures of 2-, 3-, and 4-deuteriopyridine, 2-, 3-, and 4-trimethylsilylpyridine, or 2-, 3-, and 4-methylthiopyridine indicates successful metallation of pyridine with a 1:1 mixture of BuLi-ButOK in tetrahydrofuran-hexane at -100 deg C.
- Verbeek, Jacob,George, Albert V. E.,Jong, Robertus L. P. de,Brandsma, Lambert
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p. 257 - 258
(2007/10/02)
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