Chemoselective <i>N</i>- and <i>O</i>-Difluoromethylation of 2-Pyridones, Isoquinolinones, and Quinolinones with TMSCF<sub>2</sub>Br
Ziyue Zhu, Vinayak Krishnamurti, Xanath Ispizua‐Rodriguez, Colby Barrett, G. K. Surya Prakash
Abstract
An operationally simple protocol for direct N- and O-difluoromethylation of 2-pyridones, quinolinones, and isoquinolinones using commercially available TMSCF2Br is disclosed. The chemoselectivity is modulated by simple variations in temperature, solvent, and strength of the base. Diverse, synthetically relevant functional groups are tolerated, including functional groups that have reported reactivity with TMSCF2Br. Gram-scale reactions to prepare both N- and O-difluoromethyl compounds are included.
Topics & Concepts
ChemoselectivityChemistryCombinatorial chemistryReactivity (psychology)SolventOrganic chemistryCatalysisPathologyMedicineAlternative medicineFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsInorganic Fluorides and Related Compounds