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Development of Shelf-Stable Reagents for Electrophilic Trifluoromethylthiolation Reaction

  • Zhongyan Huang
  • Norio ShibataEmail author
Chapter

Abstract

Pharmaceutical and agrochemical companies are interested in fluorinated compounds as a promising source of drug candidates. About 25% of marketed pharmaceuticals and 40% of agrochemicals contain fluorine atom(s) in their chemical structures. Therefore, the development of efficient synthetic methodology for organofluorine compounds is an important task for synthetic chemists in the field of medicinal chemistry. Among a variety of fluorinated compounds, we discuss herein trifluoromethylthio (SCF3) compounds. The SCF3 group is one of the most lipophilic functional groups in organic chemistry. The electron-withdrawing effect of the SCF3 group is similar to that of the popular trifluoromethyl (CF3) group. Hence, the replacement of the CF3 moiety in market drugs and drug candidates by a SCF3 group is a potential strategy to control bioavailability and cell-membrane permeability of original compounds. In recent decades, a large number of reports for the synthesis of SCF3 compounds have been appeared. Among them, direct trifluoromethylthiolation reaction using shelf-stable reagents is obviously attractive since this functionalization can be performed at a late stage of the multistep synthesis of target molecules. Currently, several shelf-stable reagents for electrophilic trifluoromethylthiolation have been developed. We herein introduce our recent contributions for the development of efficient, shelf-stable reagents for electrophilic trifluoromethylthiolation reaction. Design, synthesis and reactivity of two novel shelf-stable reagents, trifluoromethanesulfonyl hypervalent iodonium ylide and its diazo-derivative are discussed.

Keywords

Trifluoromethylthio Electrophilic Fluorine Sulfur Trifluoromethyl Ylide 

Notes

Acknowledgements

The author would like to thank all our collaborators and coauthors listed in the original papers. These studies were financially supported in part by the Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) Japan, the Japan Agency for Medical Research and Development (AMED), the Advanced Catalytic Transformation (ACT-C) from the Japan Science and Technology (JST) Agency, the Hoansha Foundation, and the Kobayashi International Scholarship Foundation. Mr. Zhongyan Huang thanks the Hori Sciences & Arts Foundation (Japan) for support.

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Copyright information

© Springer Nature Singapore Pte Ltd. 2017

Authors and Affiliations

  1. 1.Department of Frontier Materials, Department of Nanopharmaceutical Sciences, Life Science and Applied ChemistryNagoya Institute of TechnologyNagoyaJapan

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