Work

Transition-metal-free defluorinative cyclization of perfluoroalkyl alkenyl iodides with C,N-dinucleophiles: Synthesis of (E)-perfluoroalkenyl pyrroles

Year: 2024

Type: article

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 two fold C (sp 3 )–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.

Source: Green Synthesis and Catalysis

DOI: 10.1016/j.gresc.2024.10.002

Authors: Yu-Lan Chen, Wen-Jun Ji, Yuan-Yuan Ren, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu

Institutions: Nanjing Tech University, Nanjing Forestry University

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, Nanjing Tech University

Awards: G4592531866, G5114055651