1126-80-3Relevant articles and documents
A highly efficient palladium-catalyzed one-pot synthesis of unsymmetrical aryl alkyl thioethers under mild conditions in water
Wang, Liang,Zhou, Wei-You,Chen, Sheng-Chun,He, Ming-Yang,Chen, Qun
, p. 839 - 845 (2012)
A palladium-catalyzed, one-pot synthesis of unsymmetrical aryl alkyl thioethers involving aryl halides (aryl bromides and chlorides), thiourea and alkyl bromides has been realized under mild conditions (room temperature to 50 °C) in water with polyoxyethanyl α-tocopheryl sebacate (PTS) as amphiphile. The PTS/water could be recycled in up to eight runs without an obvious change in its activity. Copyright
Reactivity of a β-diketiminate-supported magnesium alkyl complex toward small molecules
Ren, Wenshan,Zhang, Shaohui,Xu, Ziyi,Ma, Xuebing
, p. 3109 - 3115 (2019)
The reactivity of the magnesium alkyl {[HC(C(Me)N-2,6-iPr2C6H3)2]Mg(nBu)}2 (1) toward various small molecules provides access to a variety of magnesium derivatives. For example, the insertion of elemental chalcogens (S8 and Se8) into the Mg-C bond of complex 1 gives the dimeric magnesium thiolate {[HC(C(Me)N-2,6-iPr2C6H3)2]Mg(μ-SnBu)}2 (2), magnesium selenolate [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(SenBu)(THF) (3), and magnesium diselenolate [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(Se2nBu)(THF) (4). Meanwhile, compound 4 can be readily obtained by further insertion of one selenium atom into complex 3. Moreover, the reactions of complex 1 with diphenyl dichalcogenides (PhSSPh and PhSeSePh) by σ bond metathesis afford the corresponding magnesium phenyl chalcogenolates [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(EPh)(THF) (E = S 5, Se 6) concomitant with PhEnBu release. Furthermore, the treatment of complex 1 with benzonitrile and phenyl isothiocyanate produces the serendipitous magnesium-1-azaallyl complex [HC(C(Me)N-2,6-iPr2C6H3)2]Mg(N(H)C(Ph)CHC3H7)(DME) (7) and the diimino-thioamidato magnesium compound {κ3-N,N′,N′′-(ArNCMe)2[N(Ph)CS]CH}Mg[(Ph)NC(nBu)S] (8) (Ar = 2,6-iPr2C6H3). In addition, deprotonation occurs between compound 1 and 1-methylimidazole to generate the imidazolyl complex {[HC(C(Me)N-2,6-iPr2C6H3)2]Mg(μ-Im)}2 (9) (Im = 2-N-methylimidazolyl). These results indicated that the butylmagnesium complex 1 possesses high activity toward small molecules and revealed several unusual transformations. All the new compounds were characterized by various spectroscopic methods, and their solid-state structures were further confirmed by single-crystal X-ray diffraction analyses.
The effect of inert salts on the structure of the transition state in the SN2 reaction between thiophenoxide ion and butyl chloride
Westaway, Kenneth Charles,Gao, Ying,Fang, Yao-ren
, p. 3084 - 3089 (2003)
The effect of inert salts on the structure of the transition state has been determined by measuring the secondary α deuterium and the chlorine leaving group kinetic isotope effects for the SN2 reaction between n-butyl chloride and thiophenoxide ion in both methanol and DMSO. The smaller secondary α deuterium isotope effects and very slightly larger chlorine isotope effects found in both solvents when the inert salt is present suggests that the SN2 transition state is tighter and more product-like, with a shorter S - Cα and very a slightly longer Cα - Cl bond when the added salt is present. The salt effect on the reaction in methanol where the reacting nucleophile is the solvent-separated ion-pair complex is much greater than the salt effect on the reaction in DMSO where the reacting nucleophile is the free ion. This greater change in transition-state structure found when the inert salt is present in methanol is consistent with the solvation rule for SN2 reactions. The greater change in the S - Cα bond is predicted by the bond strength hypothesis. A rationale for the changes found in transition-state structure when the inert salt is present is suggested for both the free-ion and the ion-pair reactions.
Copper oxide nanoparticles supported on graphene oxide-Catalyzed S-arylation: An efficient and ligand-free synthesis of aryl sulfides
Kamal, Ahmed,Srinivasulu, Vunnam,Murty,Shankaraiah, Nagula,Nagesh, Narayana,Reddy, T. Srinivasa,Subba Rao
, p. 2297 - 2307 (2013)
Copper oxide nanoparticles that are supported on graphene oxide as a catalytic system have been utilized for ligand-free and solvent-free C-S cross-coupling reactions with weak bases such as tri- ethylamine. Symmetrical/unsymmetrical aryl sulfides have been synthesized by the coupling of different aryl halides with aromatic as well as aliphatic sulfides. Surprisingly, aryl chlorides also well reacted with different types of sulfides in the presence of dimethyl sulfoxide and cesium carbonate. Besides, this catalytic system is suitable for the synthesis of phenothiazines via cascade C-S and C-N cross-coupling of ortho-dihalides and ortho-aminobenzothiazoles. In addition, this alternative approach is extremely useful for the synthesis of a variety of symmetrical diaryl sulfides by using thiourea as a sulfur source that is devoid of the foul smell of thiols. Indeed, the calculated E-factor value of our present protocol is 2.52. Furthermore, this protocol is particularly attractive as an environmentally benign and practical method for the synthesis of different aryl sulfides. Moreover, the heterogeneous catalytic system described in this process represents not only a greener approach but retains its significant activity for up to six catalytic cycles.
Reductive cleavage of S-S bond by Zn/AlCl3 system: A novel method for the synthesis of sulfides from alkyl tosylates and disulfides
Movassagh, Barahman,Mossadegh, Amir
, p. 1685 - 1690 (2004)
Alkyl and aryl disulfides are reduced by zinc powder in the presence of AlCl3 in aqueous media to yield zinc thiolates. This thiolate anion species then react with alkyl tosylates to give sulfides in high execellent yields.
The reaction between diphenyliodonium iodide and disulfides in the presence of a Zn/AlCl3 system: A convenient method for the synthesis of organic sulfides
Movassagh, Barahman,Mossadegh, Amir
, p. 2275 - 2278 (2005)
A convenient method for the synthesis of alkyl aryl- and diaryl sulfides by the reaction of diphenyliodonium iodide and disulfides in the presence of Zn/AlCl3 system in acetonitrile is reported. Copyright Taylor & Francis Inc.
Reductive cleavage of S-S bond by Zn/AlCl3 system: A novel method for the synthesis of sulfides from alkyl tosylates and disulfides
Movassagh, Barahman,Mossadegh, Amir
, p. 2337 - 2343 (2004)
Alkyl and aryl disulfides are reduced by zinc powder in the presence of AlCl3 in aqueous media to yield zinc thiolates. These thiolate anion species then react with alkyl tosylates to give sulfides in high to excellent yields.
Efficient CuO-nanoparticle-catalyzed C-S cross-coupling of thiols with iodobenzene
Rout, Laxmidhar,Sen, Tamal K.,Punniyamurthy, Tharmalingam
, p. 5583 - 5586 (2007)
Cheap but good: Readily available CuO nanoparticles are not only less expensive than other catalysts used for the C-S cross-coupling of thiols with aryl halides, but they are also effective at a moderate temperature and low concentration. The title reaction proceeds with a variety of alkyl and aryl thiols to give the corresponding sulfides in high yields (see scheme).
Rhodium-catalyzed carbonylative coupling of alkyl halides with thiols: a radical process faster than easier nucleophilic substitution
Ai, Han-Jun,Rabeah, Jabor,Brückner, Angelika,Wu, Xiao-Feng
supporting information, p. 1466 - 1469 (2021/02/21)
How to make a carbonylative coupling faster than the easier nucleophilic substitution? In this communication, a rhodium-catalyzed radical-based carbonylative coupling of alkyl halides with thiolphenols has been realized. Thioesters were isolated in good y
Photoinduced syntheses and reactivities of phosphorus-containing interelement compounds
Yamamoto, Yuki,Tanaka, Ryo,Ota, Miyuto,Nishimura, Misaki,Tran, Cong Chi,Kawaguchi, Shin-Ichi,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya
, p. 14708 - 14719 (2020/11/13)
The photoinduced reactions of tetraphenyldiphosphine disulfide with a range of organic dichalcogenides successfully afforded a series of phosphorus(V)-chalcogen interelement compounds via a radical process. The relative reactivities of the organic dichalcogenides (i.e., (PhS)2, (PhSe)2, and (PhTe)2) toward the PIII or PV groups in the diphosphine analogues under light were investigated in detail, and a convenient method was developed to form P-S or P-Se interelement compounds from tetraphenyldiphosphine disulfide and (PhS)2 or (PhSe)2 upon photoirradiation. Furthermore, the relative photochemical properties and reactivities of tetraphenyldiphophine (P- P interelement compound) and its analogues toward photoinduced radical addition reactions were also discussed. The formed P-E (E = S, Se) interelement compounds could be utilized for ionic reactions, and they could be transformed into various phosphine reagents via one-pot processes.
Ullmann-type: N-arylation of anilines with alkyl(aryl)sulfonium salts
Tian, Ze-Yu,Zhang, Cheng-Pan
supporting information, p. 11936 - 11939 (2019/10/11)
A palladium/copper-cocatalyzed Ullmann-type N-arylation of anilines using alkyl(aryl)sulfonium triflates as arylation reagents has been accomplished. The reaction enabled Caryl-S bond cleavage over Calkyl-S bond breakage of alkyl(aryl)sulfoniums by Pd(P(tBu)3)2/CuI and gave the corresponding N-arylated products in good to high yields. It was also significant that the reactions of aniline with asymmetric butyl(mesityl)(aryl)sulfonium triflates showed excellent selectivity, in which the aryl groups other than the bulky and electron-rich mesityl moieties were transformed.
