64740-40-5

Upstream product

• 6937-97-9 allyl(benzyl)sulfide 
• 1589-82-8 phenylmagnesium bromide 
• 100-39-0 benzyl bromide 
• 66660-08-0 ((3-iodopropyl)thio)benzene 
• 100-68-5 methyl-phenyl-thioether 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 3360-41-6 4-phenyl-butan-1-ol 
• 108-98-5 thiophenol 
• 112775-09-4 4-phenylbutyl 4-methylbenzenesulfonate 
• 34884-33-8 (phenylthio)-methylenetriphenylphosphorane 
• 104-53-0 3-phenyl-propionaldehyde 
• 67004-76-6 phenyl(4-phenylbut-1-enyl)sulfane 
• 768-56-9 4-Phenylbut-1-ene 
• 10031-93-3 ethyl 4-phenylbutyrate 

Downstream Products

• 67653-36-5 C₁₆H₁₆OS 
• 150763-59-0 phenyl 1,2,3,4-tetrahydronaphthalen-1-yl sulfide 

Relevant academic research and scientific papers

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.

Pummerer Cyclization Revisited: Unraveling of Acyl Oxonium Ion and Vinyl Sulfide Pathways

Two viable pathways (vinyl sulfide and acyl oxonium ion) for the Pummerer cyclization have been unraveled that expand the reaction scope and capabilities. Use of Br?nsted-enhanced Lewis acidity was key to realization of the vinyl sulfide pathway, whereas selective complexation of the sulfur lone pair facilitated the unprecedented acyl oxonium ion pathway. Preliminary mechanistic investigations support these hypotheses. A range of substrates have been explored to understand the reaction parameters.

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.

New efficient nickel- and palladium-catalyzed cross-coupling reactions mediated by tetrabutylammonium iodide

(formula presented) The addition of Bu4NI has been found to accelerate the palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates. Remarkably, it further allows a new nickel(0)-catalyzed cross-coupling between functionalized benzylic zinc reagents and primary alkyl iodides leading to polyfunctional products in good yields under mild reaction conditions (0-20 °C, 4-16 h).

Hole transfer promoted hydrogenation: One-electron oxidation as a strategy for selective reduction of π-bonds

One-electron oxidation is developed as a strategy for selective and efficient reduction of relatively ionizable functionalities, including conjugated dienes, styrenes, vinyl sulfides, aromatics, and even strained σ-bonds. Reduction is highly sensitive to substrate ionizability and permits selective reduction of the more ionizable function in a difunctional context. Ionization of the substrates to cation radicals is effected via the mild hole transfer agent tris(4-bromophenyl)aminium hexachloroantimonate, and subsequent reduction of the cation radicals is accomplished by tributyltin hydride. The new reduction conditions provide a novel route for generating free radicals which may prove useful in the field of radical cyclizations. This is especially attractive in the case of phenyl vinyl sulfides since the phenylthio group, which remains intact subsequent to cyclization, provides versatile functionality for further synthetic operations.

TITANIUM TETRACHLORIDE PROMOTED REDUCTION OF ALKENYL SULFIDES USING TRIETHYLSILANE AS A REDCING AGENT

Alkenyl sulfides were reduced to the corresponding alkyl sulfides with triethylsilane in the presence of titanium tetrachloride in good yields.The reduction proceeds via -phenylthio-alkyltitanium intermediate.