13910-18-4

Upstream product

• 112-29-8 1-bromo dodecane 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 4551-15-9 phenylthiotrimethylsilane 
• 17712-09-3 (Decane-1-sulfinyl)-benzene 
• 1002-69-3 decyl chloride 
• 174501-65-6 1-butyl-3-methylimidazolium Tetrafluoroborate 
• 591-50-4 iodobenzene 
• 143-10-2 decylthiol 
• 108-86-1 bromobenzene 
• 2050-77-3 Iododecane 
• 882-33-7 diphenyldisulfane 
• 161742-26-3 S-decyl thiobenzoate 
• 100-68-5 methyl-phenyl-thioether 

Downstream Products

• 96550-93-5 (decane-1-sulfonyl)benzene 
• 89665-62-3 ((R)-Decane-1-sulfinyl)-benzene 
• 131513-76-3 α-Chlorodecyl phenyl sulfide 
• 17712-09-3 (Decane-1-sulfinyl)-benzene 
• 119010-67-2 (1-But-3-enyloxy-decylsulfanyl)-benzene 
• 119010-73-0 (1-Allyloxy-decylsulfanyl)-benzene 
• 119010-69-4 [1-((E)-5-Hexyloxy-pent-3-enyloxy)-decylsulfanyl]-benzene 
• 102589-74-2 4-Decylmercapto-benzophenon 
• 18414-75-0 n-decyltrimethylsilane 

Relevant academic research and scientific papers

Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters

Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.

Facile Thiol–Ene Click Protocol Using Benzil as Sensitizer and White LED as Light Source

The thiol–ene reaction leading to a series of thioether derivatives by simple metal and oxidant free visible light promoted photosensitized protocol, following anti-Markonikov hydrothiolation of unactivated aryl and alkyl olefins at room temperature is demonstrated. Benzil served as a green photosensitizer in this reaction and white LED lights as a light source. This radical based thiol–ene reaction is operationally simple and tolerates a wide variety of functional groups present in olefins.

Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides

A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.

Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts

A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.

Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides

A new reductive preparation of unsymmetrical sulfides from esters and thiols in the presence of InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 as the reductant was developed. This protocol was applied to not only benzoic acid esters that have a methoxy, methyl, chloro, bromo, iodo, or trifluoromethyl group on the aromatic ring but also aliphatic acid esters with either aromatic or aliphatic thiols. A reaction mechanism is proposed by using Hammett plot results and several control experiments. The reductive preparation of unsymmetrical sulfides from esters and thiols by using InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 was developed. Several mechanistic studies support that the present transformation proceeds through O,S-and S,S-acetals as the reaction intermediates. TMDS = 1,1,3,3-tetramethyldisiloxane, R = aliphatic group.

Gold-Catalyzed Anti-Markovnikov Selective Hydrothiolation of Unactivated Alkenes

Despite the widespread use of transition-metal catalysts in organic synthesis, transition-metal-catalyzed reactions of organosulfur compounds, which are known as catalyst poisons, have been difficult. In particular, the transition-metal-catalyzed addition of organosulfur compounds to unactivated alkenes remains a challenge. A novel gold-catalyzed hydrothiolation of unactivated alkenes is presented, which proceeds effectively to give the anti-Markovnikov-selective adducts in good yields and in a regioselective manner.

Synthesis of unsymmetrical sulfides using ethyl potassium xanthogenate and recyclable copper catalyst under ligand-free conditions

The synthesis of unsymmetrical sulfides has been achieved in good to excellent yields with inexpensive ethyl potassium xanthogenate via cross-coupling reaction using recyclable CuO nanoparticles under ligand-free conditions.The copper oxide nanoparticles can be recovered and reused up to five cycles without loss of activity.

Nano-CuFe2O4 as a magnetically separable and reusable catalyst for the synthesis of diaryl/aryl alkyl sulfides via cross-coupling process under ligand-free conditions

An efficient protocol was developed for the CuFe2O4 nanopowder-catalyzed aryl-sulfur bond formation between aryl halide and thiol/disulfide. A variety of aryl sulfides were synthesized in impressive yields with good chemoselectivity and functional group tolerance in the presence of a catalytic amount of CuFe2O4, Cs2CO 3 as base, in nitrogen atmosphere, under ligand-free conditions, in DMSO as solvent at 100 °C. The catalyst is air-stable, inexpensive, magnetically separable and recyclable up to four cycles.

Recyclable iron/graphite catalyst for c-s cross coupling of thiols with aryl halides under ligand-free conditions

A recyclable iron/graphite (Fe/Cg) catalyst for the efficient C-S cross-coupling of various iodoarenes with aromatic/aliphatic thiols has been developed under ligand-free conditions (26 examples, up to 99% yield). The catalyst can be easily recovered and recycled up to seven cycles without loss of activity. Georg Thieme Verlag Stuttgart.

Indium-catalyzed C-S cross-coupling of aryl halides with thiols

Indium-catalyzed C-S cross-coupling of aromatic and alkane thiols with aryl halides proceeds smoothly in the presence of In(OTf)3 (10 mol %), TMEDA (20 mol %), and KOH as a base in DMSO at 135 °C. When this protocol was utilized, a variety of thiols could be cross-coupled with aryl halides to afford the corresponding aryl sulfides in good to excellent yields.