56819-77-3Relevant academic research and scientific papers
Stereoselective carbon-carbon bond formation via 1,2-asymmetric induction by a β-substituent in the reaction of α-chloro sulfides with organozinc reagents
Raghavan,Raju Chowhan
, p. 327 - 339 (2019/05/21)
The stereoselectivity of C-C bond formation in the reaction of o-chlorosulfides with a variety of organozinc reagents has been investigated. The study reveals excellent 1,2-asymmetric induction by a β-siloxy substituent and moderate 1,2-induction by the β
Pd(II) Complexes Ligated by 1,3-Bis(diphenylphosphino)calix[4]arene: Preparation, X-ray Structures, and Catalyses
Hirasawa, Kengo,Tanaka, Shinya,Horiuchi, Takeru,Kobayashi, Takahiro,Sato, Takumi,Morohashi, Naoya,Hattori, Tetsutaro
, p. 420 - 427 (2016/02/19)
syn-1,3-Bis(diphenylphosphino)-2,4-dimethoxycalix[4]arene (7) was synthesized via an Ullmann-type phosphinoylation of the syn-1,3-bis(triflate ester) (2) of p-tert-butylcalix[4]arene, followed by reduction of the phosphinoyl moieties and subsequent methylation of the remaining hydroxy groups. The treatment of diphosphine 7 with 2 molar equiv of PdCl2(MeCN)2 in benzonitrile afforded di-μ-chloro-bridged dinuclear palladium complex 8, formulated as Pd2(7)Cl4, whereas the same reaction conducted in acetonitrile with 1 molar equiv of PdCl2(MeCN)2 yielded mononuclear palladium complex 9, formulated as [Pd(7)Cl(MeCN)]Cl. Complex 9 was transformed into dicationic complex 11, formulated as [Pd(7) MeCN)2](BF4)2, by treatment with AgBF4 in dichloromethane, followed by the addition of acetonitrile. On the other hand, refluxing complex 9 in 1,2-dichloroethane yielded neutral complex 12, formulated as Pd(7)Cl2. In each of the mononuclear complexes, the palladium ion adopts a tetracoordinated square-planar geometry perpendicular to the mean plane defined by the macrocycle, and two phosphorus atoms occupy trans coordination sites. Consequently, an acetonitrile or chlorine ligand coordinates through the cavity of the calixarene, while another acetonitrile or chlorine ligand occupies the exo position. Dicationic complex 11 promoted Suzuki-Miyaura coupling between aryl chlorides and phenylboronic acid and the ring-opening reaction of an epoxide with thiophenol.
Tandem base-free synthesis of β-hydroxy sulphides under ultrasound irradiation
Lv, Guang-Shu,Duan, Fu-Jun,Ding, Jin-Chang,Cheng, Tian-Xing,Gao, Wen-Xia,Chen, Jiu-Xi,Wu, Hua-Yue
, p. 1057 - 1062 (2013/03/13)
Rongalite promotes cleavage of diaryl disulphides generating the corresponding thiolate species in situ which then undergo facile ring-opening of epoxides in a regioselective manner under ultrasound irradiation, affording β-hydroxy sulphides in good to ex
JandaJel as a polymeric support to improve the catalytic efficiency of immobilized-1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions
Lanari, Daniela,Ballini, Roberto,Bonollo, Simona,Palmieri, Alessandro,Pizzo, Ferdinando,Vaccaro, Luigi
supporting information; experimental part, p. 3181 - 3186 (2011/12/04)
JandaJel, with its greater spacing between the linear polymeric chains compared to that of polystyrene matrices, is a very efficient support for improving the catalytic efficiency of TBD under SolFC. The Royal Society of Chemistry.
Rongalite promoted highly regioselective synthesis of β-hydroxy sulfides by ring opening of epoxides with disulfides
Guo, Wenxue,Chen, Jiuxi,Wu, Dengze,Ding, Jinchang,Chen, Fan,Wu, Huayue
experimental part, p. 5240 - 5243 (2009/11/30)
Rongalite promotes cleavage of disulfides generating thiolate anions that then undergo facile ring opening of epoxides in the presence of K2CO3 to afford α-addition products 3 with good to excellent yields. The important f
Ionic liquid promoted regio- and stereo-selective thiolysis of epoxides-A simple and green approach to β-hydroxy- and β-keto sulfides
Ranu, Brindaban C.,Mandal, Tanmay,Banerjee, Subhash,Dey, Suvendu S.
, p. 278 - 283 (2008/02/11)
A variety of epoxides underwent facile cleavage by thiols under the catalysis of 1-methyl-3-butylimidazolium bromide, [bmIm]Br, to produce the corresponding β-hydroxy sulfides with high regio- and stereo-selectivity. On the other hand, a specially designed basic ionic liquid, [bmIm]OH, efficiently catalyzes the thiolysis of ,β-epoxy ketones providing β-keto sulfides through simultaneous retro-aldol cleavages. The reactions are clean, high yielding, and do not require any organic solvent. The catalyst is also recycled. CSIRO 2007.
Indium(I) iodide promoted cleavage of dialkyl disulfides - Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides
Ranu, Brindaban C.,Mandal, Tanmay
, p. 762 - 770 (2007/10/03)
Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding β-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably fast. Thus, simple and convenient procedures for the synthesis of β-ketosulfides or β-cyanosulfides and β-hydroxyalkyl sulfides have been developed using this cleavage reaction.
Efficient, eco-friendly and regioselective method for thiolysis of 1,2-epoxides with diaryl disulfides in the presence of Zn/Bi(TFA) 3-TBPB or Zn/Bi(OTf)3-TBPB
Khosropour, Ahmad R.,Khodaei, Mohammad M.,Ghozati, Kazem
, p. 572 - 576 (2007/10/03)
Diaryl disulfides undergo regioselective ring-opening of 1,2-epoxides in the presence of zinc powder and 3-4 mol-% of bismuth(III) trifluoroacetate or 1 mol-% of bismuth(III) triflate in molten tetrabutylphosphonium bromide (TBPB) to afford the correspond
BiCl3 catalyzed thiolyzation reaction of 1,2-epoxides with diaryl disulfides in the presence of zinc powder and ionic liquid
Khosropour,Khodaei,Ghozati
, p. 2525 - 2531 (2007/10/03)
A new and efficient method has been developed for the regio- and chemoselective synthesis of β-hydroxysulfides with the ring-opening reaction of 1,2-epoxides by diaryl disulfides and zinc powder in the presence of a catalytic amount of BiCl3 in
Thiolysis of 1,2-epoxides by thiophenol catalyzed under solvent-free conditions
Fringuelli, Francesco,Pizzo, Ferdinando,Tortoioli, Simone,Vaccaro, Luigi
, p. 6785 - 6787 (2007/10/03)
Thiolysis of alkyl- and aryl-1,2-epoxides was investigated under solvent-free conditions in the presence of Lewis and Br?nsted acid and base catalysts (InCl3, p-TsOH, n-Bu3P, K2CO3). Five mol% of catalyst was su
