7133-25-7Relevant academic research and scientific papers
Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles
Gellert, Beate A.,Kahlcke, Nils,Feurer, Markus,Roth, Stefanie
supporting information; experimental part, p. 12203 - 12209 (2011/11/07)
Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.
Silica nanoparticles as a reusable catalyst: A straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts under neutral reaction conditions
Banerjee, Subhash,Das, Jayanta,Alvarez, Richard P.,Santra, Swadeshmukul
experimental part, p. 302 - 306 (2010/06/13)
A simple and straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts has been demonstrated using silica nanoparticles (NPs) as a reusable catalyst via the 1,2-addition of thiols to alkenes, alkynes and alkyl/acyl halides, and the 1,4-addition of thiols to conjugated alkenes at room temperature.
Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases
Rioz-Martinez, Ana,De Gonzalo, Gonzalo,Pazmino, Daniel E. Torres,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 6409 - 6416 (2011/02/24)
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
Native silica nanoparticle catalyzed anti-Markovnikov addition of thiols to inactivated alkenes and alkynes: a new route to linear and vinyl thioethers
Banerjee, Subhash,Das, Jayanta,Santra, Swadeshmukul
scheme or table, p. 124 - 127 (2009/04/14)
A new route for the synthesis of linear and vinyl thioethers has been demonstrated using bare silica nanoparticle as catalyst at room temperature under solvent-free conditions. The catalyst can be reused up to six times without loss of catalytic activity.
Ionic liquid promoted regio- And stereoselective addition of thiols to alkynes and alkenes under organic solvent free condition - A green reaction
Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Ghosh, Sudip,Jana, Ranjan
experimental part, p. 1199 - 1204 (2009/12/31)
A simple ionic liquid, l-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF4, promotes anti-Markovnikov addition of thiols to alkynes providing (Z)- and (E)-vinyl sulfides stereoselectively. The addition of thiols to alkenes in presence of another ionic liquid, [pmim]Br proceeds through anti-Markovnikov manner, whereas the addition to vinyl ethers and acetates occurs at more electrophilic C-2 position adjacent to oxygen. The products are obtained in high yields.
Water-promoted highly selective anti-Markovnikov addition of thiols to unactivated alkenes
Ranu, Brindaban C.,Mandal, Tanmay
, p. 925 - 928 (2008/02/02)
The highly selective anti-Markovnikov addition of thiols to unactivated alkenes is demonstrated in water at room temperature without any additive. This is a very simple and efficient method for the synthesis of linear thioethers. Georg Thieme Verlag Stuttgart.
A Novel Catalyst System, Trimethylsilyl Chloride and Indium(III) Chloride, as an Efficient Catalyst in the Sulfide Synthesis
Mukaiyama, Teruaki,Ohno, Takashi,Nishimura, Takashi,Han, Jeong Sik,Kobayashi, Shu
, p. 2524 - 2527 (2007/10/02)
O-Trimethylsilyl monothioacetals, which are generally difficult to activate under acidic conditions due to their rapid disproportionation, smoothly react with triethylsilane in the presence of a novel catalyst system, trimethylsilyl chloride and indium(III) chloride, to afford the corresponding sulfides in good to high yields.One pot synthesis of sulfides from aldehydes is also attained in high yields by successive treatment of aldehydes with trimethylsilyl alkyl (aryl) sulfides and triethylsilane in the presence of the above catalyst system under extremely mild conditions.
An Effective Activation of O-Trimethylsilyl Monothioacetal under Extremely Mild Conditions Using a Novel Catalyst System, Trimethylsilyl Chloride and Indium(III) Chloride
Mukaiyama, Teruaki,Ohno, Takashi,Nishimura, Takashi,Han, Jeong Sik,Kobayashi, Shu
, p. 2239 - 2242 (2007/10/02)
A novel catalyst system, trimethylsilyl chloride and indium(III) chloride, effectively catalyzes the reaction of O-trimethylsilyl monothioacetals with triethylsilane and silylated carbon nucleophiles, respectively, to afford the corresponding sulfide derivatives in good to high yields.
Ionic Hydrogenation with Organosilanes under Acid-Free Conditions. Synthesis of Ethers, Alkoxysilanes, Thioethers, and Cyclic Ethers via Organosylil Iodide and Triflate Catalyzed Reductions of Carbonyl Compounds and Their Derivatives
Sassaman, Mark B.,Prakash, G. K. Surya,Olah, George A.
, p. 3771 - 3780 (2007/10/02)
The general ether synthesis method based on the trialkylsilane/trialkylsilyl iodide or triflate reagent system has been extended to the syntheses of alkoxysilanes from ketones, tetrahydrofurans and tetrahydropyrans from dicarbonyl compounds, and thioethers by reductive cleavage of O-silylhemithioacetals.
TITANIUM TETRACHLORIDE PROMOTED REDUCTION OF ALKENYL SULFIDES USING TRIETHYLSILANE AS A REDCING AGENT
Takeda, Takeshi,Tsuchida, Toshio,Fujiwara, Tooru
, p. 1219 - 1220 (2007/10/02)
Alkenyl sulfides were reduced to the corresponding alkyl sulfides with triethylsilane in the presence of titanium tetrachloride in good yields.The reduction proceeds via -phenylthio-alkyltitanium intermediate.
