Synthesis of Difluorinated Heterocyclics through Metal-Free [8+1] and [4+1] Cycloaddition of Difluorocarbene
Yimin Jia, Yuan Yuan, Jinfeng Huang, Zhong‐Xing Jiang, Zhigang Yang
Abstract
With Ph3P+CF2COO– or TMSCF2Br as the difluorocarbene sources, a facile metal-free cycloaddition between heteroconjugated alkenes and difluorocarbene was developed for the highly convergent synthesis of novel difluorinated heterocyclics, including gem-difluorinated azetidines and 2,3-dihydrobenzofurans. The cycloaddition features high reactivity and regioselectivity, as well as good tolerance of various electron-donating or electron-withdrawing substituents on azaheptafulvenes and o-quinone methides.
Topics & Concepts
DifluorocarbeneCycloadditionRegioselectivityChemistryReactivity (psychology)Medicinal chemistryOrganic chemistryCatalysisAlternative medicinePathologyMedicineFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions