Inherent Oxygen Preference in Enolate Monofluoromethylation and a Synthetic Entry to Monofluoromethyl Ethers

Authors

  • Yoshinori Nomura,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • Etsuko Tokunaga,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • Prof. Norio Shibata

    Corresponding author
    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
    • Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • This study was supported financially in part by Grants-in-Aid for Scientific Research (B; No. 21390030, JSPS; 22106515, JSPS). We are grateful to the Central Glass Co., Ltd. for support.

Abstract

original image

Erwarte das Unerwartete: Die stabilen Salze 1, X=OTf, PF6, x=2, y=1, ermöglichen die inhärent selektive elektrophile O-Alkylierung von Enolaten mit einer Monofluormethylgruppe und eröffnen so den Zugang zu Monofluormethylethern, die durch direkte elektrophile Fluormethylierung von Alkoholen nur schwierig zugänglich sind. 1, X=BF4, x=0, y=3, dagegen liefert C-alkylierte Produkte.

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