C[BOND]O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols

Authors

  • Peter E. Maligres,

    Corresponding author
    1. Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)
    • Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)
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    • These authors contributed equally to this work.

  • Jing Li,

    Corresponding author
    1. Department of Discovery Process Chemistry, Merck Research Laboratories, West Point, PA 19486 (USA)
    • Department of Discovery Process Chemistry, Merck Research Laboratories, West Point, PA 19486 (USA)
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    • These authors contributed equally to this work.

  • Shane W. Krska,

    1. Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)
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  • John D. Schreier,

    1. Department of Discovery Chemistry, Merck Research Laboratories, West Point, PA 19486 (USA)
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  • Izzat T. Raheem

    Corresponding author
    1. Department of Discovery Chemistry, Merck Research Laboratories, West Point, PA 19486 (USA)
    • Department of Discovery Chemistry, Merck Research Laboratories, West Point, PA 19486 (USA)
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    • These authors contributed equally to this work.


  • We thank Prof. Stephen L. Buchwald and Michael Palucki for helpful discussions and Janine Noelle Brouillette for her contribution to the NMR structure elucidaton.

Abstract

original image

A robust and general catalyst system facilitates the alkoxylation of activated heteroaryl halides with primary, secondary, and select tertiary alcohols without the need for an excess of either coupling partner (see scheme). This catalyst system displays broad functional-group tolerance and excellent regioselectivity, and is insensitive to the order of reagent addition.

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