Synthesis of 5-Fluoro-dihydroindolizines from Pyrrole-2-acetic Acids and Trifluoromethyl Alkenes via Dual C–F Bond Cleavage in a CF<sub>3</sub> Group
Zhengchang Sun, Lei Zhou
Abstract
Herein, we describe the synthesis of 5-fluoro-dihydroindolizines via dual C–F bond cleavage in a trifluoromethyl group. The photocatalytic defluorinative coupling of pyrrole-2-acetic acids and α-trifluoromethyl alkenes cleaved the first C–F bond, providing gem-difluoroalkenes bearing an unprotected pyrrole motif. Subsequently, an intramolecular SNV reaction closed the ring by forming a C–N bond concomitantly with the cleavage of the second C–F bond. Using indole-2-acetic acids as the substrates, the reactions also allow the assembly of 6-fluoro-dihydropyrido[1,2-a]indoles.
Topics & Concepts
ChemistryTrifluoromethylPyrroleIntramolecular forceAcetic acidBond cleavageCleavage (geology)Indole testMedicinal chemistryStereochemistryOrganic chemistryCatalysisEngineeringAlkylFracture (geology)Geotechnical engineeringFluorine in Organic ChemistrySynthesis and Reactivity of HeterocyclesCyclopropane Reaction Mechanisms