Palladium‐Catalyzed Carbon–Fluorine and Carbon–Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes

Wenyi Chen, Thomas N. Hooper, Jamues Ng, Andrew J. P. White, Mark R. Crimmin

doi:10.1002/anie.201706378

Palladium‐Catalyzed Carbon–Fluorine and Carbon–Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes

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Wenyi Chen

Department of Chemistry Imperial College London South Kensington London SW7 2AZ UK
Thomas N. Hooper

Department of Chemistry Imperial College London South Kensington London SW7 2AZ UK
Jamues Ng

Department of Chemistry Imperial College London South Kensington London SW7 2AZ UK
Andrew J. P. White

Department of Chemistry Imperial College London South Kensington London SW7 2AZ UK
Mark R. Crimmin

Department of Chemistry Imperial College London South Kensington London SW7 2AZ UK

書誌事項

公開日: 2017-08-30

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/anie.201706378

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Through serendipitous discovery, a palladium bis(phosphine) complex was identified as a catalyst for the selective transformation of sp<jats:sup>2</jats:sup>C−F and sp<jats:sup>2</jats:sup>C−H bonds of fluoroarenes and heteroarenes to sp<jats:sup>2</jats:sup>C−Al bonds (19 examples, 1 mol % Pd loading). The carbon–fluorine bond functionalization reaction is highly selective for the formation of organoaluminium products in preference to hydrodefluorination products (selectivity=4.4:1 to 27:1). Evidence is presented for a tandem catalytic process in which hydrodefluorination is followed by sp<jats:sup>2</jats:sup>C−H alumination.</jats:p>