Recent Progress on Direct Trifluoromethylthiolating Reagents and Methods

doi:10.6023/A17050202

Acta Chim. Sinica ›› 2017, Vol. 75 ›› Issue (8): 744-769.DOI: 10.6023/A17050202 Previous Articles Next Articles

Review

直接三氟甲硫基化试剂及方法的研究进展

张盼盼, 吕龙, 沈其龙

有机氟化学重点实验室中国科学院上海有机化学研究所中国科学院大学上海 200032

投稿日期:2017-05-09 发布日期:2017-08-16
通讯作者: 沈其龙,E-mail:shenql@mail.sioc.ac.cn E-mail:shenql@mail.sioc.ac.cn
作者简介:张盼盼,男,中国科学院上海有机化学研究所在读博士生,主要从事亲电三氟甲硫基化试剂的开发以及小分子三氟甲硫基化反应的研究;吕龙,男,1991年获中国科学院上海有机化学研究所博士学位,1993年至1996年在世界氟化学研究中心美国杜邦公司研究与发展中心和衣阿华大学从事博士后研究.现主要从事新型含氟砌块的设计、合成及反应研究、含氟功能材料以及新农药的创制等研究工作;沈其龙,男,1996年7月本科毕业于南京大学环境科学与工程系;1999年7月硕士毕业于上海有机化学研究所;2002年7月毕业于美国麻省大学Dartmouth分校,获理学硕士学位;2002年9月至2007年9月就读于美国耶鲁大学,获哲学博士学位.
基金资助:
项目受国家自然科学基金（Nos.21625206，21632009，21372247，21572258，21572259，21421002）和中国科学院战略性先导科技专项（B类）（No.XDB20000000）资助.

Recent Progress on Direct Trifluoromethylthiolating Reagents and Methods

Zhang Panpan, Lu Long, Shen Qilong

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032

Received:2017-05-09 Published:2017-08-16
Contact: 10.6023/A17050202 E-mail:shenql@mail.sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21625206,21632009,21372247,21572258,21572259,21421002) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No.XDB20000000).

With a significantly high Hansch's hydrophobicity parameter (π=1.44), electron-withdrawing trifluoromethylthio group (CF₃S-) has been considered as one of the most lipophilic substituents and privileged fragments that are able to improve drug molecules' pharmacokinetic and physicochemical properties such as lipophilicity and metabolic stability. It is well-known that incorporation of the trifluoromethylthio group into small molecules greatly enhances its ability to cross lipid membranes and in vivo absorpotion rate. In addition, the high electronegativity of the trifluoromethylthio group significantly improves the small molecule's stablity in acidic environments. Not surprisingly, the trifluoromethylthio group has been of special attention not only from the academia but also from pharmaceutical and agrochemical industry for their use in isostere-based drug design. Development of highly efficient methods for the introduction of the trifluoromethylthio group into small molecules, thereafter, has become a subject of recent focus in the field of organic chemistry. In the early 1960s, a few methods for the formation of trifluoromethylthioethers were reported, which typically involved halogen exchange of the trichloromethyl-substituted compounds and trifluoromethylation of thiolated substrates. However, the conditions of these methods were harsh and incompatible with many common functional groups. Since 2008, new reagents and methods that were able to efficiently incorporate the trifluoromethylthio group under mild conditions have emerged, that pave the way for the facile introduction of trifluoromethylthio group into site-specific positions of the target molecules. In this review, we will first briefly introduce the indirect strategies for trifluoromethylthiolation including halogen exchange and trifluoromethylation of thiolated substrates, and then focus on the direct trifluoromethylthiolation strategies including the transition metal-catalyzed trifluoromethylthiolation reactions, electrophilic trifluoromethylthiolation reactions with electrophilic trifluoromethylthiolating reagents and radical trifluoromethylthiolations. These methods represent the most straightforward and promising approaches for the incorporation of the trifluoromethylthio group into small molecules. At the end, we will discuss the remaining problems and challenges in this particular field.

Key words: fluorine chemistry, trifluoromethylthiolation, indirect strategy, direct method

Cite this article

Zhang Panpan, Lu Long, Shen Qilong. Recent Progress on Direct Trifluoromethylthiolating Reagents and Methods[J]. Acta Chim. Sinica, 2017, 75(8): 744-769.

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直接三氟甲硫基化试剂及方法的研究进展

Recent Progress on Direct Trifluoromethylthiolating Reagents and Methods

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