OMS-2 for Aerobic, Catalytic, One-pot Alcohol Oxidation-Wittig Reactions: Efficient Access to α,β-Unsaturated Esters

Authors

  • Jagadeswara R. Kona,

    1. Department of Chemistry, University of Connecticut, 55 N Eagleville Road, Storrs, CT 06269 (USA), Fax: (+1) 860-486-2981
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  • Dr. Cecil K. King'ondu,

    1. Department of Chemistry, University of Connecticut, 55 N Eagleville Road, Storrs, CT 06269 (USA), Fax: (+1) 860-486-2981
    2. Department of Sustainable Energy Science and Engineering, Nelson Mandela African Institution of Science and Technology, P. O. Box 447, Arusha (Tanzania)
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  • Prof. Amy R. Howell,

    Corresponding author
    1. Department of Chemistry, University of Connecticut, 55 N Eagleville Road, Storrs, CT 06269 (USA), Fax: (+1) 860-486-2981
    • Department of Chemistry, University of Connecticut, 55 N Eagleville Road, Storrs, CT 06269 (USA), Fax: (+1) 860-486-2981

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  • Prof. Steven L. Suib

    Corresponding author
    1. Department of Chemistry, University of Connecticut, 55 N Eagleville Road, Storrs, CT 06269 (USA), Fax: (+1) 860-486-2981
    2. Institute of Materials Science, University of Connecticut, 97 N Eagleville Road, Storrs, CT 06269 (USA)
    • Department of Chemistry, University of Connecticut, 55 N Eagleville Road, Storrs, CT 06269 (USA), Fax: (+1) 860-486-2981

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Abstract

Manganese oxide octahedral molecular sieve (OMS) materials with well-defined pores have been extensively studied over two decades due to their intriguing chemical and physical properties. OMS-2, the synthetic cryptomelane form of manganese oxide, was synthesized by a modified reflux method and was found to be highly active for obtaining α,β-unsaturated esters (up to 95 % yield and with high diastereoselectivities) from a variety of benzyl, heteroaryl, allyl and alkyl alcohols via one-pot alcohol oxidation-Wittig reaction. The transformation utilizes air as the stoichiometric oxidant, and the inexpensive catalyst can be recovered and reused.

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