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

doi:10.6023/cjoc202103042

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3134-3143.DOI: 10.6023/cjoc202103042 Previous Articles Next Articles

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Sc(OTf)₃催化的δ-三氟甲基-δ-芳基-双取代对亚甲基苯醌和硫醇的反应: 高效合成二芳基甲烷硫醚化合物

李华^a, 庞靖祥^c, 刘华铮^b, 赵长印^b, 李松^b, 王恒山^a^,^*(), 刘希功^b^,^*()

a 广西师范大学化学与药学学院药用资源化学与药物分子工程国家重点实验室广西民族医药协同创新中心桂林 541004
b 山东大学化学与化工学院济南 250100
c 山东第一医科大学药物研究所&山东省医学科学院山东省医药生物技术中心山东省罕见病重点实验室国家卫生委员会生物技术药物重点实验室济南 250000

收稿日期:2021-03-23 修回日期:2021-04-19 发布日期:2021-05-25
通讯作者: 王恒山, 刘希功
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21801093); 国家自然科学基金(21977021); 国家自然科学基金(81760626); 中国博士后科学基金(2019M662321)

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^a, Jingxiang Pang^c, Huazheng Liu^b, Changyin Zhao^b, Song Li^b, Hengshan Wang^a(), Xigong Liu^b()

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

Received:2021-03-23 Revised:2021-04-19 Published:2021-05-25
Contact: Hengshan Wang, Xigong Liu
About author:
† (These authors contributed equally to this work).
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.

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Sc(OTf)₃催化的δ-三氟甲基-δ-芳基-双取代对亚甲基苯醌和硫醇的反应: 高效合成二芳基甲烷硫醚化合物

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

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