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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 8: 3134 - 3143

DOI: https://doi.org/10.6023/cjoc202103042

ARTICLES

Sc(OTf)3-Catalyzed 1,6-Conjugate Addition of Thiols to δ-CF3-δ-aryl-disubstituted para-Quinone Methides: Efficient Construction of Diarylmethane Thioethers

  • Hua Li ,
  • Jingxiang Pang ,
  • Huazheng Liu ,
  • Changyin Zhao ,
  • Song Li ,
  • Hengshan Wang ,
  • Xigong Liu
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  • a State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004
    b School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100
    c Shandong Medicinal Biotechnology Centre, Key Laboratory for Rare & Uncommon Diseases of Shandong Province, Key Lab for Biotech-Drugs of National Health Commission, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250000
† (These authors contributed equally to this work).
*Corresponding authors.E-mail: ;
E-mail:

Received date: 2021-03-23

  Revised date: 2021-04-19

  Online published: 2021-05-25

Supported by

National Natural Science Foundation of China(21801093); National Natural Science Foundation of China(21977021); National Natural Science Foundation of China(81760626); China Postdoctoral Science Foundation(2019M662321)

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Abstract

An efficient and practical 1,6-conjuate addition reaction of δ-CF3-δ-aryl-disubstituted para-quinone methides with thiols has been described. This approach provides a straightforward access to structurally diverse diarylmethane thioethers bearing CF3-substituted quaternary stereocenters using 5 mol% Sc(OTf)3 as catalyst. The reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both δ-CF3-δ-aryl-disubstituted para-quinone methides and thiophenols. Moreover, alkyl thioalcohols and benzylmercaptan have proven to be suitable substrates. Diarylmethane thioethers belong to an important structural scaffold that widely exists in a number of bioactive molecules and trifluoromethyl group has a profound effect on physiological properties of organic molecules. Therefore, the efficient method for the synthesis of diarylmethane thioethers bearing CF3-substituted quaternary stereocenters might provide a powerful strategy for the discovery of biologically interesting agents.

Key words： δ-CF3-δ-aryl-disubstituted; para-quinone methides; diarylmethane; thioethers; 1,6-conjuate addition

Cite this article

Hua Li , Jingxiang Pang , Huazheng Liu , Changyin Zhao , Song Li , Hengshan Wang , Xigong Liu . Sc(OTf)3-Catalyzed 1,6-Conjugate Addition of Thiols to δ-CF3-δ-aryl-disubstituted para-Quinone Methides: Efficient Construction of Diarylmethane Thioethers[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3134 -3143 . DOI: 10.6023/cjoc202103042

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