Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.
J Org Chem. 2010 Jun 4;75(11):3626-43. doi: 10.1021/jo1004179.
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.
顺式-1,2-环己二醇（L3）已被证明是一种高效、多功能的双齿 O-供体配体，可为 Cu 催化体系提供高活性。它比反式-1,2-环己二醇或乙二醇等二醇更有效。这种商业可得的顺式-1,2-环己二醇配体促进了烷基、芳基或杂环硫醇与烷基、芳基、杂环或取代的乙烯基卤化物的 Cu 催化交叉偶联反应。该新型催化体系促进了生物重要的乙烯基硫化物的温和、高效的立体和区域选择性合成。使用这种催化剂体系，电子丰富的取代乙烯基硫化物的产率通常为 75-98%。最重要的是，这种单一的催化剂体系非常通用，可以获得广泛的硫化物。鉴于其温和的反应条件、简单性、通用性和对官能团的出色耐受性，该方法尤其值得注意。
