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Regioselective C–H Trifluoromethylation of Aromatic Compounds by Inclusion in Cyclodextrins

preprint
submitted on 06.03.2021, 04:34 and posted on 08.03.2021, 13:22 by Xu Lu, Ryohei Kawazu, Jizhou Song, Yusuke Yoshigoe, Takeru Torigoe, Yoichiro Kuninobu
A regioselective radical C–H trifluoromethylation of aromatic compounds was developed using cyclodextrins (CDs) as additives. The C–H trifluoromethylation proceeded with high regioselectivity to afford the product in good yield, even on the gram scale. In the presence of CDs, some substrates underwent a single trifluoromethylation selectively, whereas mixtures of single- and double-trifluoromethylated products were formed in the absence of the CD. 1H NMR experiments indicated that the regioselectivity was controlled by the inclusion of a substrate inside the CD cavity.

Funding

JSPS KAKENHI JP 17H03016

JSPS KAKENHI JP 18H04656

JSPS KAKENHI JP 20H04824

Takeda Science Foundation

The Mitsubishi Foundation

Yamada Science Foundation

History

Email Address of Submitting Author

kuninobu@cm.kyushu-u.ac.jp

Institution

Kyushu University

Country

Japan

ORCID For Submitting Author

0000-0002-8679-9487

Declaration of Conflict of Interest

The authors declare no competing financial interests.

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