14905-79-4

Usage

InChI:InChI=1/C10H14S/c1-3-9(2)11-10-7-5-4-6-8-10/h4-9H,3H2,1-2H3

Upstream product

• 67456-50-2 (sec-butylsulfinyl)benzene 
• 63866-84-2 sec-Butyldiphenylarsanoxid 
• 930-69-8 sodium thiophenolate 
• 13133-62-5 thiophenolate 
• 78-76-2 s-butyl bromide 
• 874-79-3 phenyl(propyl)sulfide 
• 74-88-4 methyl iodide 
• 108-98-5 thiophenol 
• 591-50-4 iodobenzene 
• 882-33-7 diphenyldisulfane 
• 917-54-4 methyllithium 
• 1822-73-7 phenylthioethylene 
• 66783-99-1 sodium 2-butanethiolate 
• 513-48-4 2-butyl iodide 

Downstream Products

• 67456-50-2 (sec-butylsulfinyl)benzene 
• 76003-63-9 2-[(1-methylpropyl)thio]benzoic acid 
• 1246438-81-2 (R_S,R_C)-(1-methylpropylthio)benzene-S-oxide 
• 1246438-83-4 (R_S,S_C)-(1-methylpropylthio)benzene-S-oxide 
• 1246438-84-5 (S_S,R_C)-(1-methylpropylthio)benzene-S-oxide 
• 1246438-82-3 (S_S,S_C)-(1-methylpropylthio)benzene-S-oxide 
• 3019-19-0 tert-butyl phenyl sulfide 
• 882-33-7 diphenyldisulfane 
• 4170-72-3 tert-butyl-phenyl sulfone 
• 34009-06-8 (±)-(sec-butylsulfonyl)benzene 

Relevant academic research and scientific papers

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C?S Formation

Sulfur-containing molecules are of utmost topical importance towards the effective development of pharmaceuticals and functional materials. Herein, we present an efficient and mild electrochemical thiolation by cross-electrophile coupling of alkyl bromide

Novel and facile procedure for the synthesis of Ni(II) and Pd(II) PSCOP pincer complexes. Evaluation of their catalytic activity on C-S, C-Se and C-C cross coupling reactions

A new and facile procedure for the synthesis of non-symmetric phosphinito-thiophosphinito PSCOP pincer complexes based on Ni(II) and Pd(II) was developed. The synthesis of the complexes was carried out in a single step, starting from 3,3-dihydroxydiphenyldisulfide. The Ni(II) complexes were tested as catalysts in C-S and C-Se coupling reactions, being the tBu derivative 3-Ni the one exhibiting the best performance in both transformations. In this case, the sterics of the substrates was studied, showing that higher steric hindrance leads to lower yields. Analogously, the Pd(II) complexes were used as catalyst in Suzuki-Miyaura couplings of para-substituted bromobenzenes and phenyl boronic acid, being the analogous tBu derivative complex 3-Pd the best catalysts for this process, exhibiting tolerance to a wide range of functional groups.

C[sbnd]S cross-coupling catalyzed by a series of easily accessible, well defined Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)]

The synthesis, characterization and catalytic evaluation of a series of NHC-Ni(II) complexes 1-Ni (-Me), 2-Ni (-nBu) and 3-Ni (-Bn) bearing a phthalimide fragment and a cyclopentadienyl (Cp) ligand is reported. The complexes were evaluated in C

One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents

Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.

CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides

We report a general copper-catalyzed cross-coupling of thiols with aryl halides by using N-aryl-N′-alkyl oxalic diamide (L3) or N,N′-dialkyl oxalic diamide (L5) as the ligand. Both aryl and alkyl thiols can be coupled with unactivated aryl bromides and chlorides to give the desired products in good yields. Furthermore, this system features a broad substrate scope and good tolerance of functional groups. Importantly, the oxalic diamides are stable and can be prepared easily from commercially available and cheap starting materials.

Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent

One of the most widely used methods of preparation of organolithium compounds is by the reductive lithiation of alkyl phenyl thioethers or, usually less conveniently, alkyl halides with either aromatic radical-anions of lithium or lithium metal in the presence of an aromatic electron-transfer catalyst. Here we present results showing that lithium dispersion can achieve reductive lithiation in the absence of the electron-transfer agent. This procedure is more efficient, and surprisingly, the order of reactivity of substrates is reversed depending on whether the electron-transfer agent is present or absent. For example, in the presence of a preformed radical-anion, tert-butyl phenyl sulfide cleaves significantly faster than methyl phenyl sulfide, whereas in the absence of the radical-anion, it is just the opposite. Density functional theory calculations reveal that the exothermicity of the cleavage of the C-S bond in alkyl phenyl thioethers on the lithium surface is dependent on the size of the alkyl group, the smaller the alkyl group the greater the exothermicity. The increased reactivity is attributed to the smaller steric repulsion between the alkyl group and the lithium surface. The methodology includes, but may not be limited to, the lithium dispersion reductive lithiation of phenyl thioethers, alkyl chlorides, acrolein diethyl acetal, and isochroman.

Microwave-assisted C-C and C-S couplings catalysed by organometallic PD-SCS or coordination NI-SNS pincer complexes

A family of SCS and SNS pincer compounds of the type [PdCl{C6H3-2,6-(CH2SR)2}] {R = tBu (3a), sBu (3b), iBu (3c)} and [NiCl2{C5H3N-2,6-(CH2SR)2}] {R = tBu (4a), sBu (4b)} have been prepared. Among these, complexes 3b, 3c, 4a-4c are reported for the first time. Dimeric compounds such as [NiCl{C5H3N-2,6-(CH2SiBu)2}μ-Cl]2 (4c) were found in the solid state for the nickel complexes with lower steric hindrance exhibiting octahedral metal centers, whereas other nickel structures such as [NiCl2{C5H3N-2,6-(CH2StBu)2}(iPrOH)] (4d) could also expand their coordination number by coordinating to solvents. The single crystal X-ray diffraction results for 4a, 4c and 4d are presented. The catalytic activity of the six compounds was studied in C-C and C-S cross-coupling reactions under conventional heating and under microwave irradiation conditions. The palladium catalysts enabled good to excellent conversions in Suzuki-Miyaura couplings of p-substituted halobenzenes with phenylboronic acid. Comparable yields resulted from application of the nickel complexes in the thioetherification of iodobenzene with different disulfides. The fast increase in reaction temperature associated with microwave irradiation, in combination with the robust pincer catalysts, allowed for quantitative conversions in only minutes.

Lithium-titanium exchange of tertiary α-sulfonyl carbanions: Synthesis, structure, dynamics and reactivity of bis(1-sulfonylalkyl) titaniums

Lithium-titanium exchange of tertiary α-sulfonyl carbanions with ClTi(OiPr)3 and Cl2Ti(OiPr)2 in diethyl ether gave bis(1-sulfonylalkyl) titaniums and not the corresponding (1-sulfon-ylalkyl) titaniums. X-ray crystal structure analysis of di(iso-propoxy) bis[1-(phenylsulfonyl) cyclobutyl]titanium and di-(isopropoxy) bis[1-(phenylsulfonyl) isopropyl]titanium showed asymmetric distorted octahedral complexes, having hexaco-ordinate Ti atoms, two C-Ti bonds, four Ti-O bonds, and two four-membered Ti-O-S-Cα rings. According to 1H NMR spectroscopy bis(1-sulfonylcycloalkyl) titaniums are non-flux-ional at room temperature. This suggests that chiral bis(1-sulfonylalkyl) titaniums should be configurationally stable. The bis(1-sulfonylalkyl) titaniums are stable at room temperature towards β-H elimination. They selectively add to benzaldehyde in the presence of acetophenone but do not react with methyl iodide. The reaction of tertiary acyclic α-sulfonyl carbanions with ClTi(OiPr)3 in tetrahydrofuran (THF) gives different titanium derivatives with unspecified structures, which not only selectively react with benzaldehyde in the presence of acetophenone but are also alkylated by methyl iodide.

Pinacol as a new green reducing agent: Molybdenum-catalyzed chemoselective reduction of sulfoxides and nitroaromatics

Pinacol is disclosed as a new chemoselective and environmentally benign reducing agent for sulfoxides and nitroaromatics assisted by readily available dichlorodioxomolybdenum(VI) complexes as catalysts. A wide range of substrates including those bearing challenging functional groups has been efficiently and selectively reduced with acetone and water being the only by-products of these reactions. Copyright

Experimental and theoretical investigation of the enantiomerization of Lithium α-tert-butylsulfonyl carbanion salts and the determination of their structures in solution and in the crystal

Dynamic NMR (DNMR) spectroscopy of [R1C(R2)SO 2R3]Li (R1, R2 = alkyl, phenyl; R3 = Ph, tBu, adamantyl, CEt3) in [D8]THF has shown that the S-tBu, S-adamantyl, and S-CEt3 derivatives have a significantly higher enantiomerization barrier than their S-Ph analogues. C α-S bond rotation is most likely the rate-determining step of the enantiomerization of the salts bearing a bulky group at the S atom and two substituents at the Cα atom. Ab initio calculations on [Me(Ph)- SO 2tBu]- gave information about the two Cα-S rotational barriers, which are dominated by steric effects. Cryoscopy of [R1C(R 2)SO2tBu]Li in THF at -108°C revealed the existence of monomers and dimers. X-ray crystal structure analysis of the monomers and dimers of [R1C(R2)SO2tBu]Li·L n (R1 = Me, Et, tBuCH2, PhCH2, tBu; R2 = Ph, L = THF, 12-crown-4, PMDTA) and [R1C(R 2)SO2Ph]Li·2diglyme [R1 = R2 = Me, Et; R1-R2 = (CH2)5] showed them to be O-Li contact ion pairs (CIPs). The monomers and dimers have a Cα-S conformation in which the lone-pair orbital at the Cα atom bisects the O-S-O angle and a significantly shortened Cα-S bond. The Cα atom of [R1C(R2)SO2R 3]Li·Ln (R1 = Ph; R3 = Ph, tBu) is planar, whereas the Cα atom of [R1C(R 2)SO2R3]Li·Ln (R1 = R2 = alkyl) is strongly pyramidalized in the case of R3 = Ph and most likely planar for R3 = tBu. Ab initio calculations on [MeC- (Me)SO2R]- gave a pyramidalized Cα atom for R = Me and a nearly planar one for R = CF3 and tBu. The [R1C(R 2)SO2-tBu]Li salts were characterized by 1H, 13C, and 6Li NMR spectroscopy. 1H{ 1H} and 6Li{1H} NOE experiments are in accordance with the existence of O-Li CIPs. 1H and 13C NMR spectroscopy of [R1C(R2)SO2tBu]Li in [D 8]THF at low temperatures showed equilibrium mixtures of up to five different species being most likely monomeric and dimeric O-Li CIPs with different configurations. According to 7Li NMR spectroscopy, the addition of HMPA to [MeC(Ph)SO2tBu]Li in [D8]THF at low temperatures causes the formation of the separated ion pair [MeC(Ph)SO 2tBu]Li(HMPA)4.