A very active cu-catalytic system for the synthesis of aryl, heteroaryl, and vinyl sulfides.
cis-1,2-Cyclohexanediol (L3) has been shown to be an efficient and versatile bidentate O-donor ligand that provides a highly active Cu-catalytic system. It was more effective than diols such as trans-1,2-cyclohexanediol or ethylene glycol. This commercially available cis-1,2-cyclohexanediol ligand facilitated the Cu-catalyzed cross-coupling reactions of alkyl, aryl, or heterocyclic thiols with either alkyl, aryl, heterocyclic, or substituted vinyl halides. This new catalytic system promoted the mild and efficient stereo- and regiospecific synthesis of biologically important vinyl sulfides. The yields obtained using electron-rich substituted vinyl sulfides with this catalyst system are generally 75-98%. Most importantly, this singular catalyst system is extremely versatile and provides entry into a wide range of sulfides. This method is particularly noteworthy given its mild reaction conditions, simplicity, generality, and exceptional level of functional group tolerance.
Kabir
M Shahjahan
MS
Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.
Lorenz
Michael
M
Van Linn
Michael L
ML
Namjoshi
Ojas A
OA
Ara
Shamim
S
Cook
James M
JM
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003511:Cyclohexanols; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis; D008722:Methods; D013440:Sulfides / Q000138:chemical synthesis*; D014753:Vinyl Compounds / Q000138:chemical synthesis
D003511:Cyclohexanols; D006841:Hydrocarbons, Aromatic; D013440:Sulfides; D014753:Vinyl Compounds; D003300:Copper; C064619:1,2-cyclohexanediol