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Synthesis 2023; 55(19): 3090-3103
DOI: 10.1055/a-2096-6929
DOI: 10.1055/a-2096-6929
paper
Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry
Palladium-Catalyzed Hydroalkylation of Alkoxyallenes Using Monofluorinated Nucleophiles
The financial support from the National Key Research and Development Program of China (2021YFC2102400), the National Natural Science Foundation of China (22171087), the Science and Technology Innovation Plan of Shanghai Science and Technology Commission (21N41900500, 20JC1416900), the Fundamental Research Funds for the Central Universities, and the open foundation of Hubei Key Laboratory of Quality Control of Characteristic Fruits and Vegetables (2022K004) is highly appreciated. J.-S.Y. also acknowledges financial support from the ‘Zijiang Scholar Program’ of East China Normal University.
Abstract
A branch-selective hydroalkylation of alkoxyallenes with monofluorinated nucleophiles was developed using palladium catalysis, allowing construction of valuable α-monofluoroalkylated allylic ethers. Notably, this represents the first catalytic hydrofluoroalkylation of alkoxyallenes. The practicability of this method is highlighted by its broad substrate scope and diversified product elaborations. Initial investigation of the asymmetric variant could afford chiral fluorine-containing allylic ethers with up to 68% ee.
Key words
palladium catalysis - alkoxyallenes - hydrofluoroalkylation - branch-selectivity - fluorineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2096-6929.
- Supporting Information
Publication History
Received: 09 April 2023
Accepted after revision: 22 May 2023
Accepted Manuscript online:
22 May 2023
Article published online:
27 June 2023
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