175349-36-7

Upstream product

• 103-19-5 di(p-tolyl) disulfide 
• 10521-91-2 5-phenylpentan-1-ol 
• 14469-83-1 (5-bromopentyl)benzene 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 5285-74-5 4-tolyl thiocyanate 

Downstream Products

• 175349-37-8 1-(1-Chloro-5-phenyl-pentylsulfanyl)-4-methyl-benzene 
• 828-14-8 (E)-hex-4-en-1-ylbenzene 
• 103387-41-3 1,6-diphenyl-hex-1-ene 
• 175349-38-9 1-chloro-5-phenylpentyl p-tolyl sulfoxide 
• 420110-25-4 1-chloro-1-methyl-5-phenylpentyl p-tolyl sulfoxide 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides

The cross-electrophile coupling between unactivated alkyl bromides with arenesulfonyl cyanides catalyzed by Ni(acac)2under reductive conditions to form unsymmetrical sulfides is developed. This approach for sulfide synthesis is practical, relies on available, unfunctionalized materials such as alkyl (pseudo)halides, and is scalable. This catalytic strategy provides a complementary method for the preparation of unsymmetrical alkyl-aryl sulfides under mild conditions with good functional group tolerance.

A method for generation of α-halo carbanions (carbenoids) from aryl α-haloalkyl sulfoxides with alkylmetals

Ligand exchange reaction of simple aryl α-haloalkyl sulfoxides with alkyllithium and ethylmagnesium halide at low temperature was investigated. On treatment of aryl α-haloalkyl sulfoxide with n-BuLi, t-BuLi, or EtMgX exclusively sulfur-alkyl bond-cleavage took place to afford α-halo carbanion (carbenoid). When this reaction was carried out without a proton source, the intermediate α-halo carbanion decomposed to give olefines in good yield. The ligand exchange reaction of sulfoxide was found to be very fast and the reaction could be carried out with a proton or a deuterium source (internal quench) to afford alkyl halide. This procedure offers a new method for preparing α-deuterated) halides (the halogen is F, Cl, or Br).