Chinese Journal of Organic Chemistry >
Cu(OTf)2 Catalyzed Conjugate Addition of Mercaptans to Enones
Received date: 2020-12-14
Revised date: 2020-12-06
Online published: 2021-02-26
Supported by
Nanjing Agricultural University Research Start-Up Funding, the Jiangsu Shuang Chuang Doctoral Grants in 2019, and the National Program for Student Innovation through Research and Training in 2020(202010307090)
Thioether is a class of compounds with important biological and physiological activities, especially for drugs and natural products, and its efficient synthesis method is one of the research hotspots in organic chemistry. Thia-Michael addition, especially the addition catalyzed by small organic molecules has been widely proved to be an effective method for synthesizing thioether molecules. However, very few studies on transition metal-catalyzed thia-Michael addition have been published and further exploration in this area is needed. In this work, different types of thiol molecules have been effectively added to various cyclic and linear Michael acceptors through the catalysis of copper(II) triflate. To our delight, 42 kinds of sulfide molecules (up to 99% yield) have been efficiently synthesized. This method has many advantages such as mild reaction conditions, wide substrates, simple operation and excellent yield, providing a new method for the preparation of various thioether molecules.
Key words： copper catalysis; conjugate addition; mercaptan
Tongfei Zhang , Yibo Chen , Zhenbo Gao . Cu(OTf)2 Catalyzed Conjugate Addition of Mercaptans to Enones[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2424 -2434 . DOI: 10.6023/cjoc202012022
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