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Updated: May 10, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Palladium-catalysed regio- and stereo-controlled C-2 β-fluorovinylation of indoles
Atul K Chaturvedi1, Alastair J J Lennox1
1School of Chemistry, University of Bristol Cantock's Close Bristol BS8 1TS UK a.lennox@bristol.ac.uk.
Abstract:
Vinyl-fluorides appended to heterocycles are a broadly underdeveloped family of functionality with potential application in bioactive compounds. Herein, we disclose a C-H functionalisation strategy for the regio- and stereo-controlled synthesis of Z-β-fluorovinyl indoles exclusively in the C-2 position. Z-Fluorovinyl iodonium salts, which are formed from alkynes through a Ag-catalysed process, engage in a palladium-catalysed C-2 C-H functionalisation of indoles (and pyrroles) to achieve a broad scope of β-fluorovinyl heterocycles in good to excellent yields. Mechanistic studies and product derivatisations are provided.
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