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Iridium-Catalyzed 1,3-Hydrogen Shift/Chlorination of Allylic Alcohols

Authors

  • Dr. Nanna Ahlsten,

    1. Department of Organic Chemistry, Stockholm University, 10691 Stockholm (Sweden)
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    • These authors contributed equally to this work.

  • Dr. Antonio Bermejo Gómez,

    1. Department of Organic Chemistry, Stockholm University, 10691 Stockholm (Sweden)
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    • These authors contributed equally to this work.

  • Prof. Dr. Belén Martín-Matute

    Corresponding author
    1. Department of Organic Chemistry, Stockholm University, 10691 Stockholm (Sweden)
    • Department of Organic Chemistry, Stockholm University, 10691 Stockholm (Sweden)

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  • Financial support from the Swedish Research Council (Vetenskapsrådet), the Knut and Alice Wallenberg Foundation, and the Department of Organic Chemistry at Stockholm University is gratefully acknowledged.

Abstract

original image

Tandem: Allylic alcohols react with N-chlorosuccinimide (NCS) in a tandem 1,3-H shift/C[BOND]Cl bond formation leading to α-chloroketones and α-chloroaldehydes. The reactions proceed with complete selectivity to give single constitutional isomers of monochlorinated carbonyl compounds. The utility of the transformation is illustrated by the straightforward synthesis of 4,5-disubstituted 2-aminothiazoles from allylic alcohols.

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