Abstract
Functionalization of the C-F bond in perfluoroalkyl substances represents an emerging focus in organic chemistry. We report here a transition-metal-free intermolecular defluorinative cyclization of perfluoroalkyl alkenyl iodides with C,N-dinucleophiles. This method enables highly chemo-, regio-, and stereoselective 2-fold C (sp3)-F bond cleavage at two vicinal carbon centers in the perfluoroalkyl chain, resulting in the assembly of a five-membered N-heterocycle with a structurally privileged (E)-prefluoroalkenyl unit. The success of partial defluorination is mainly attributed to the pre-installed alkenyl functionality and iodide atom in perfluoroalkyl substances.
Original language | English |
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Journal | Green Synthesis and Catalysis |
DOIs | |
State | Accepted/In press - 2024 |
Keywords
- C-F bond functionalization
- Defluorinative cyclization
- Heterocycles
- Perfluoroalkyl alkene
- PFASs
- Pyrrole
- Transition-metal-free conditions