<i>N</i>-Selective Difluoromethylation of 4-Hydroxyquinolines
<i>N</i>-selective difluoromethylation of 4-hydroxyquinolines is a formidable challenge due to competing <i>N</i>- and <i>O</i>-difluoromethylation pathways. Herein, we present a mild, efficient, and scalable protocol using BrCF<sub>2</sub>CO<sub>2</sub>H and LiO<sup><i>t</i></sup>Bu for the selective <i>N</i>-difluoromethylation of 4-hydroxyquinolines. This method tolerates reactive functional groups such as carboxylic acid, ester, and amide. A series of <i>N</i>-deuterodifluoromethyl analogues (-CF<sub>2</sub>D) is also synthesized.
Authors
- Kishore Natte (ORCID: https://orcid.org/0000-0001-8557-1969)
- Sandeep Kumawat (ORCID: https://orcid.org/0009-0008-1410-4536)
- Pavel K. Mykhailiuk (ORCID: https://orcid.org/0000-0003-1821-9011)
- Sebastian Wohlrab (ORCID: https://orcid.org/0000-0003-1407-7263)
- Taras M. Tarasiuk (ORCID: https://orcid.org/0000-0001-6318-1361)
- Tetyana Yegorova
- Gopika N. Nair
- Venkata Narayana Kalevaru
Institutions
- Taras Shevchenko National University of Kyiv (UA)
- Leibniz Institute for Catalysis (DE)
- Enamine (Ukraine) (UA)
- Indian Institute of Technology Hyderabad (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-08
- DOI
- https://doi.org/10.1021/acs.orglett.5c03246
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00