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Palladium-Catalyzed Aromatic Azidocarbonylation

Authors

  • Fedor M. Miloserdov,

    1. The Institute of Chemical Research of Catalonia, Avgda. Països Catalans 16, 43007 Tarragona (Spain)
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  • Prof. Vladimir V. Grushin

    Corresponding author
    1. The Institute of Chemical Research of Catalonia, Avgda. Països Catalans 16, 43007 Tarragona (Spain)
    • The Institute of Chemical Research of Catalonia, Avgda. Països Catalans 16, 43007 Tarragona (Spain)
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  • We thank Drs. Jordi Benet-Buchholz, Eduardo C. Escudero-Adán, Marta Martínez Belmonte, and Eddy Martin for single-crystal X-ray diffraction studies and Prof. Piet W. N. M. van Leeuwen and Maxim A. Novikov for helpful discussions. The ICIQ Foundation and Consolider Ingenio 2010 (Grant CSD2006-0003) are thankfully acknowledged for support of this research.

Abstract

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Aryl iodides smoothly react with NaN3 and CO in the presence of a Pd/Xantphos catalyst to give aroyl azides (ArCON3) in 75–92 % yield. The reaction occurs under mild reaction conditions (1 atm, 20–50 °C) and exhibits high functional-group tolerance. (Xantphos=9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene)

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