Shandong Science ›› 2020, Vol. 33 ›› Issue (6): 55-63.doi: 10.3976/j.issn.1002-4026.2020.06.008

• New Materials • Previous Articles     Next Articles

Bi(OTf)3 catalyzed thia-Michael addition of vinyl thioethers to ortho-Qinone Methides: an efficient access to ortho-hydroxybenzyl thioethers

SHI Xin-hua1PENG Dan1WANG Feng1MU Qiu-hong1LI Jin-hui1YU Yi-tao1,ZHAO Ning1,LI Bing1,ZHANG Shuo1*,LIU Lin2*   

  1. 1.Shandong Provincial Key Laboratory of Special Silicon-Containing Materials, Advanced Materials Institute, Qilu University of Technology (Shandong Academy of Sciences),Jinan 250014,China;2. Haihe River, Huaihe River and Xiaoqinghe River basin water conservancy management and service center of Shandong Province, Jinan 250001, China
  • Received:2020-07-02 Online:2020-12-09 Published:2020-12-10

Abstract: In the present study, the Bi(OTf)3 catalyzed thia-Michael addition to ortho-quinone methides for the synthesis of ortho-hydroxybenzyl thioethers with 2-[hydroxy(phenyl)methyl phenols and vinyl thioethers in 1,2-dichloroethane was developed. The reaction could be achieved at 30 ℃ for 3 h and the products were obtained in moderate to good yields (78%~88%). The prominent features of the present strategy are good chemical selectivity and with wide substrate scope. For 2-hydroxy(phenyl)methyl phenols, electron-withdrawing groups and electron-donating groups on aromatic rings could react soothly to obtain corresponding products. Also, the reaction could be achieved with phenyl vinyl thioether and ethyl vinyl thioether. Furthermore, the reaction could be scaled up to multigram scale.

Key words: ortho-Quinone, thia-Michael addition, Bismuth(III) trifluoromethanesulfonate, vinyl thioethers , ortho-hydroxybenzyl thioethers

CLC Number: 

  • O622.7