88708-53-6

Upstream product

• 1034014-59-9 1-(dodec-1-ylsulfanyl)-2-phenylethyne 
• 536-74-3 phenylacetylene 
• 112-55-0 1-dodecylthiol 

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 

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.

Radical sequential processes promoted by 1,5-radical translocation reaction: Formation and [3 + 2] anulation of alkenesulfanyl radicals

Radical addition of 2-substituted ethanethiols 1-5 to alkyl-, dialkyl-, and phenylacetylenes affords the corresponding β-sulfanylalkenyl radicals, which can undergo 1,5-radical translocation (RT reaction) in competition with intermolecular hydrogen abstraction (HA reaction). The RT reaction is the first step of a sequential radical process leading to alkenesulfanyl radicals through an "intermolecular sulfanyl radical transaddition" from an alkene to an alkyne molecule. Alkenesulfanyl radicals can undergo a regioselective [3 + 2] anulation reaction with a CC triple bond, eventually leading to thiophene products through 5-endo cyclization of vinyl radicals onto CC double bond. The effect of the nature of ethanethiol and alkyne substituents on the RT/HA ratio has been investigated, and results will be discussed.

A CONVENIENT PREPARATION OF Z-STYRYL, Z,Z- AND E,Z-DISTYRYL SULFIDES IN LIQUID AMMONIA

Nucleophilic attack of thiols on phenylacetylene (1) in liquid ammonia at room temperature gave the corresponding Z-isomer of styryl sulfides in high yield stereoselectively.Reaction of 1 with Na2S also proceeded selectively to give Z,Z-distyryl sulfide (12).On the other hand, reaction with NaSH gave 12 besides E,Z-isomer as a minor product.