Mild LiOMe-Catalyzed Trifluoromethylation of Carbonyl Compounds

The Journal of Organic Chemistry 2026

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Authors: Santhosh Reddy Naini, Venumadhav Janganati, Arun Dixith Reddy Shada, Srinivasarao Tenneti, Srijita Bhowmik, Jonathan M. Bietsch, Praveen Kumar Gajula, Venkatarathnam Nasipireddy, Leila Terrab, Jinya Yin, Nageswara Rao Kalikinidi, Chanaka M. Amarasekarage
+12 more Sameera Siyabalapitiya Arachchige, Shanika M. P. Gamage, Nuwan Kondasinghe, Rajasekar Reddy Annapureddy, Badrinath N. Kakde, Manasa Mamunooru, Anji Chen, Zhirui Wang, Gopal Sirasani, Srinivas Achanta, B. Qu, Chris H. Senanayake
DOI: 10.1021/acs.joc.5c02246
Cited by: 0
References: 42

Abstract

We report a mild lithium methoxide (LiOMe)-catalyzed protocol for the trifluoromethylation of aldehydes, acyclic and cyclic ketones, and α,β-unsaturated carbonyl compounds. This method avoids the use of fluorinated or strong bases that promote enolization, offering broad functional group tolerance, including silyl, Boc, Cbz, nitrile, and benzyl groups, enabling its application to diverse complex substrates. Additionally, LiOMe catalyzes the diastereoselective addition of CF 3 to chiral keto esters derived from (1 R,2 S )-1-(methylamino)-2,3-dihydro-1 H -inden-2-ol, affording products with diastereomeric ratios up to 84:16.

Fields of Study & Subjects

Fluorine in Organic Chemistry Synthesis and Characterization of Pyrroles Inorganic Fluorides and Related Compounds

Publication details

Journal / source
The Journal of Organic Chemistry
Volume
91
Issue
2
Pages
1229–1239
Publication date
7 January 2026
Language
EN