88708-54-7

Upstream product

• 536-74-3 phenylacetylene 
• 112-55-0 1-dodecylthiol 
• 103-64-0 bromostyrene 
• 2757-37-1 didodecyl disulfide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 1034014-59-9 1-(dodec-1-ylsulfanyl)-2-phenylethyne 
• 637-44-5 phenylpropyolic acid 

Downstream Products

• 7206-28-2 (Z)-dodec-5-ene 
• 7206-16-8 (E)-dodec-5-ene 
• 15325-54-9 (Z)-hex-1-en-1-ylbenzene 
• 6111-82-6 (E)-1-phenyl-1-hexene 
• 18869-27-7 (E)-(2-cyclohexylvinyl)benzene 
• 40132-69-2 (Z )-1-(2-cyclohexyl-1-ethenyl)benzene 
• 15325-61-8 (E)-(3-methylbut-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Efficient visible light initiated hydrothiolations of alkenes/alkynes over Ir2S3/ZnIn2S4: Role of Ir2S3

The hydrothiolations of alkynes/alkenes with thiols is an atom-economic and thus attractive method for the constructions of C-S bonds. Here Ir2S3/ZnIn2S4 nanocomposites with varied Ir2S3 loadings were obtained by one-pot solvothermal method from ZnCl2, InCl3 and thioacetamide with IrCl3. The loading of Ir2S3 on the surface of ZnIn2S4 promoted the hydrothiolations of alkenes and alkynes, with an optimum performance observed over 0.5 molpercent Ir2S3/ZnIn2S4 nanocomposite. Based on the studies on the performance of several other cocatalysts (MoS2, NiS and Pd) loaded ZnIn2S4 and the EIS analyses, it was proposed that the superior performance over Ir2S3/ZnIn2S4 nanocomposite can be ascribed to an improved efficiency on the photogeneration of the thiyl radicals by loading Ir2S3 as well as its inactivity for photocatalytic hydrogen evolution, a side reaction in the light initiated hydrothiolation reaction over ZnIn2S4. This study not only demonstrates an efficient and green strategy to synthesize thiolated products under visible light based on semiconductor photocatalysis, but also provides some guidances for the design and development of photocatalytic systems for light induced organic syntheses.

Visible light initiated hydrothiolation of alkenes and alkynes over ZnIn2S4

The construction of C-S bonds is very important. The hydrothiolation of alkenes or alkynes with thiols represents an attractive and atom economical approach for the formation of C-S bonds. In this manuscript, flowerlike microspheres of ZnIn2S4 consisting of interweaving nanoflakes were prepared by a solvothermal method and were applied for the first time in the visible light initiated hydrothiolation of alkenes and alkynes. The reactions between a broad range of thiols and alkynes or alkenes over irradiated ZnIn2S4 afford the corresponding hydrothiolated products in moderate to excellent yields. The mechanism proposed based on the ESR results suggests that the holes generated over irradiated ZnIn2S4 are reductively quenched by the thiols to generate thiyl radicals, which are added to the alkynes/alkenes to generate alkene/alkyl radicals for the propagation of thiol-ene/thiol-yne coupling reactions. The use of solar light and a semiconductor-based photocatalyst to realize the thiol-ene and thiol-yne coupling reactions in a green solvent (methanol), with only stoichiometric thiols required and applicable to a broad substrate scope, makes this reaction protocol a green, sustainable and cost-effective strategy for the synthesis of thiolated products. This study also highlights the great potential of semiconductor-based photocatalysis for advanced organic syntheses.

Convenient and Efficient Diastereoselective Preparation of Functionalized Z-Alkenyl Sulfides

We have developed an efficient and convenient regio- and stereoselective reduction of the alkynyl sulfides with pinacolborane in the presence of copper(I) chloride to produce (Z)-alkenyl sulfides in good and very good yields. The functionalized alkynyl sulfides are readily available based on the reaction of lithium acetylides with thiotosylates under mild conditions.

Regioselective hydrothiolation of terminal acetylene catalyzed by magnetite (Fe3O4) nanoparticles

Herein, we report a new and solvent-free methodology for the preparation of vinyl thioethers from terminal alkynes and thiols, using magnetite (Fe3O4) nanoparticles as a recyclable catalyst. With this greener method, the desired viny

Sulfamic acid: An efficient and recyclable catalyst for the regioselective hydrothiolation of terminal alkenes and alkynes with thiols

Herein, we described a new method for the preparation of thioethers through hydrothiolation of alkenes and alkynes, using sulfamic acid as a reusable catalyst. Generally, this new methodology afforded the desired products in very good yields, under metal

Hydrothiolation of Alkenes and Alkynes Catalyzed by 3,4-Dimethyl-5-vinylthiazolium iodide and Poly(3,4-dimethyl-5-vinylthiazolium) iodide

The highly selective anti-Markovnikov addition of thiols to unactivated alkenes and alkynes was demonstrated by using 3,4-dimethyl-5-vinylthiazolium iodide or its polymer, poly(3,4-dimethyl-5-vinylthiazolium) iodide, as a complementary catalyst. The reaction proceeded cleanly under base-free conditions in air with both aromatic and aliphatic thiols. The polymer catalyst showed a high turnover number (≈5800) and could be reused up to four times without any loss of catalytic activity. DFT calculations supported stabilization of the thiyl radical intermediate by the thiazolium cation, which resulted in reaction of the radical with unsaturated C?C bonds.

Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols

A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO2 atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO2 atmosphere. The reaction system is robust and utilizes inexpensive, readily available substrates. A cyclic alkene/carboxylate copper complex intermediate is proposed as the key step in determining the stereoselectivity, and an equivalent amount of water is found to play an active role as a proton donor.

Efficient copper-catalyzed s-vinylation of thiols with vinyl halides

The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couplewith aryl iodides in the presence of only 0.5mol% Cu2O without the need for an ancillary liga

Synthesis of vinyl sulfides by copper-catalyzed decarboxylative C-S cross-coupling

A novel method for the synthesis of vinyl sulfides by the decarboxylative cross-coupling of arylpropiolic acids with thiols using copper(I) salts as catalysts has been developed. In the presence of CuI and Cs2CO 3, a variety of thiols reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in good to excellent yields with high stereoselectivity for Z-isomers.

Water-promoted regioselective hydrothiolation of alkynes

Water promotes hydrothiolation of unactivated alkynes efficiently without any catalyst or additive. The reaction at room temperature furnishes vinyl sulfides with high regioselectivity via anti-Markovnikov addition. The terminal al- kynes provide dithiola