Platinum-Catalyzed Direct Amination of Allylic Alcohols with Aqueous Ammonia: Selective Synthesis of Primary Allylamines

Authors

  • Dr. Kalpataru Das,

    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • Ryozo Shibuya,

    1. Graduate School of Pharmaceutical Sciences, Kyushu University, CREST, Maidashi Higashi-ku, Fukuoka 812-8582 (Japan)
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  • Yasuhito Nakahara,

    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • Nicolas Germain,

    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • Prof. Dr. Takashi Ohshima,

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, Kyushu University, CREST, Maidashi Higashi-ku, Fukuoka 812-8582 (Japan)
    • Graduate School of Pharmaceutical Sciences, Kyushu University, CREST, Maidashi Higashi-ku, Fukuoka 812-8582 (Japan)
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  • Prof. Dr. Kazushi Mashima

    Corresponding author
    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
    • Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • This work was supported by The Core Research for Evolutional Science and Technology (CREST) program of the Japan Science and Technology Agency (JST) and The Grand-in-Aid for Scientific Research on Innovative Area “Reaction Integration”, and the Uehara Memorial Foundation. K.D. and Y.N. are grateful to the Global COE Program of Osaka University for their research fellowship.

Abstract

original image

Direct amination of unactivated allylic alcohols with aqueous ammonia was catalyzed by a Pt/phosphine complex to give the corresponding allylamines along with water as the sole by-product. Under optimized reaction conditions, primary allylamines were obtained as major products with excellent monoallylation selectivity. cod=1,5-cyclooctadiene.

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