Palladium‐Catalyzed Intermolecular Dicarbofunctionalization of Unactivated Alkenes: Synthesis of Fluoroalkylated Heterocycles with All‐Carbon Quaternary Centers

The redox‐neutral palladium‐catalyzed dicarbofunctionalization of unactivated alkenes with a variety of functionalized difluoromethyl and perfluoroalkyl halide is presented here. This transformation proceeds smoothly at low temperatures and enables the assembly of diversified fluoroalkylated pyrrolo...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-01, Vol.2022 (3), p.n/a
Main Authors: Cheng, Jiajia, Zhang, Huali, Lv, Jinliang, Zheng, Jinhua
Format: Article
Language:English
Subjects:
Alkenes
All-carbon quaternary center
Carbon
Electron transfer
Fluoroalkylation
Halides
Heterocycles
Low temperature
Palladium
Palladium catalysis
Perfluoroalkyl & polyfluoroalkyl substances
Phosphines
Radical reactions
Regioselectivity
Single electrons
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Summary:The redox‐neutral palladium‐catalyzed dicarbofunctionalization of unactivated alkenes with a variety of functionalized difluoromethyl and perfluoroalkyl halide is presented here. This transformation proceeds smoothly at low temperatures and enables the assembly of diversified fluoroalkylated pyrrolo[1,2‐a]indole derivatives with one all‐carbon quaternary center in high regioselectivity. Mechanistic studies suggested an operative radical mechanism and the initiation of the inner‐sphere single electron transfer between a dual phosphine ligand‐coordinated palladium(0) species and perfluoroalkyl halides. The redox‐neutral Pd‐catalyzed dicarbofunctionalization of unactivated alkenes with a variety of functionalized perfluoroalkyl halide is presented. This transformation enables the assembly of diversified fluoroalkylated pyrrolo[1,2‐a]indoles with one all‐carbon quaternary center in high regioselectivity. Mechanistic studies suggest the generation of perfluoroalkyl radicals from the single electron reduction of palladium(0) to perfluoroalkyl halides.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101342