Mild LiOMe-Catalyzed Trifluoromethylation of Carbonyl Compounds
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<sub>3</sub> to chiral keto esters derived from (1<i>R</i>,2<i>S</i>)-1-(methylamino)-2,3-dihydro-1<i>H</i>-inden-2-ol, affording products with diastereomeric ratios up to 84:16.
Authors
- Chanaka M. Amarasekarage (ORCID: https://orcid.org/0000-0002-4294-3766)
- Jinya Yin (ORCID: https://orcid.org/0009-0003-4041-4283)
- Chris H. Senanayake (ORCID: https://orcid.org/0009-0009-3170-0687)
- Nuwan Kondasinghe
- B. Qu
- Rajasekar Reddy Annapureddy (ORCID: https://orcid.org/0000-0001-5855-4688)
- Praveen Kumar Gajula (ORCID: https://orcid.org/0009-0008-5051-4612)
- Jonathan M. Bietsch
- Badrinath N. Kakde (ORCID: https://orcid.org/0000-0003-0018-2855)
- Srinivas Achanta (ORCID: https://orcid.org/0009-0003-7334-1965)
- Gopal Sirasani
- Manasa Mamunooru
- Srijita Bhowmik (ORCID: https://orcid.org/0000-0001-5951-4557)
- Srinivasarao Tenneti (ORCID: https://orcid.org/0000-0002-6687-8348)
- Santhosh Reddy Naini (ORCID: https://orcid.org/0000-0001-7825-5810)
- Venumadhav Janganati (ORCID: https://orcid.org/0000-0003-3641-2990)
- Sameera Siyabalapitiya Arachchige (ORCID: https://orcid.org/0000-0003-4376-7415)
- Shanika M. P. Gamage
- Nageswara Rao Kalikinidi
- Anji Chen
- Arun D. R. Shada
- Zhirui Wang
- Venkatarathnam Nasipireddy
- Leila Terrab
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-01-07
- DOI
- https://doi.org/10.1021/acs.joc.5c02246
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00