A research paper titled "KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N-Sulfinylimines Using HFC-125" authored by Shibata Laboratory [Yuji Sumii (Assistant Professor), Hiroto Iwasaki (Life Science and Applied Chemistry Program, first year of the Master's Course), Yamato Fujihira (then, Life Science and Applied Chemistry Program, second year of the Master's Course), and Elsayed Maher Mahmoud Saleh (Department of Nanopharmaceutical Sciences, fourth year of the Doctoral Course)] published in The Journal of Organic Chemistry, a scientific journal published by the American Chemical Society (ACS), was highly evaluated and selected as "Supplementary Cover Art" for The Journal of Organic Chemistry Vol. 87, No. 23 (published on December 2) (Fig. 1).

　　　　　　（Figure1）

The following is a description of this highly evaluated research paper. Stereoselective pentafluoroethylation of N-sulfinylimines using HFC-125, a hydrochlorofluorocarbon (HFC) substance, and KHMDS/triglyme was successfully developed. This technique selectively synthesizes both diastereomers of the product depending on the presence of triglyme. This method has presented a direct and inexpensive alternative to the stereoselective pentafluoroethylation based on the technique using two bases (KHMDS and P₄-^tBu, which is highly expensive), which was reported previously (Fig. 2).

　　　　　　（Figure2）

The cover art (Fig. 1) was designed by a Japanese artist and is titled "SHIGERU." HFC-125 and HFC-23 are fluorine-containing greenhouse gases and industrial waste. HFCs are turned into important materials through conversion to enantioenriched fluorinated molecules. The cover represents the steady conversion of HFCs into environmentally friendly materials. This research was supported by a joint research project between Dr. Dominique Cahard (Normandie University) based on "Invitation Fellowships for Research in Japan (L22527)" under the auspices of JSPS and Tosoh Finechem Corporation, and Precise Material Science for Degradation and Stability (research supervisor: Atsushi Takahara) (Grant No.: JPMJCR21L1) under the auspices of JST CREST.

Shibata Laboratory

<Journal containing this article>
　Journal name: The Journal of Organic Chemistry

　Title: KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N-Sulfinylimines Using HFC-125

　Authors: Yuji Sumii, Hiroto Iwasaki, Yamato Fujihira, Elsayed M. Mahmoud, Hiroaki Adachi, Kagawa, Dominique Cahard and Norio Shibata

　Article information: DOI: 10.1021/acs.joc.2c01821　

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