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Mechanistic insights into silver-catalyzed intramolecular aminofluorination of activated allene

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Abstract

A study has been conducted in the silver-catalyzed intramolecular aminofluorination of activated allene with density functional theory (DFT). It contributes to the proposal that the catalytic cycle mainly contains two stages: (1) cyclization to afford a key binuclear Ag(I)–Ag(I) intermediate IM-Ag containing C–Ag(I) bond and (2) conversion of C–Ag(I) into C–F bond by N-fluorobenzenesulfonmide (NFSI). DFT studies suggest that the key C–F bond-forming reaction occurs via a novel disilver-assisted metathesis process, and this step is the rate-determining step in the whole reaction.

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Authors and Affiliations

  1. Department of Applied Chemistry, Zhejiang Gongshang University, Hangzhou, 310035, China

    Zhang Xiang

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  1. Zhang Xiang
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Correspondence to Zhang Xiang.

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Xiang, Z. Mechanistic insights into silver-catalyzed intramolecular aminofluorination of activated allene. Theor Chem Acc 136, 102 (2017). https://doi.org/10.1007/s00214-017-2134-7

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  • DOI: https://doi.org/10.1007/s00214-017-2134-7

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