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A Practical and Mild Method for the Highly Selective Conversion of Terminal Alkenes into Aldehydes through Epoxidation–Isomerization with Ruthenium(IV)–Porphyrin Catalysts

Authors

  • Jian Chen,

    1. Shanghai–Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 354 Feng Lin Road, Shanghai 200032, China
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  • Chi-Ming Che Prof. Dr.

    1. Shanghai–Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 354 Feng Lin Road, Shanghai 200032, China
    2. Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, Fax: (+852) 2857-1586
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  • We are thankful for the financial support of The University of Hong Kong (Generic Drugs Research Program), the Area of Excellence Scheme (AoE 10/01P) administered by the University Grants Council (HKSAR), and the Hong Kong Research Grants Council (HKU7099/01P). J.C. thanks the Croucher Foundation of Hong Kong for a postgraduate studentship.

Abstract

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Aldehydes in excellent yields were obtained from the ruthenium–porphyrin-catalyzed oxidation of various terminal alkenes with 2,6-dichloropyridine N-oxide under mild conditions. The aldehydes generated from these ruthenium-catalyzed alkene oxidations can be used in situ for olefination reactions with ethyl diazoacetate in the presence of PPh3 in a one-pot diazoacetate olefination starting from alkenes (see example).

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