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Brønsted Acid Catalyzed α-Alkylation of Aldehydes with Diaryl Methyl Alcohols

Authors

  • Chong Xing,

    1. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 67911961
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  • Dr. Hui Sun,

    1. State key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Rd. Dalian, 116023 (P. R. China), Fax: (+86) 0411-8467-5584
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  • Dr. Junmin Zhang,

    1. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 67911961
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  • Prof. Dr. Guohui Li,

    Corresponding author
    1. State key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Rd. Dalian, 116023 (P. R. China), Fax: (+86) 0411-8467-5584
    • State key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Rd. Dalian, 116023 (P. R. China), Fax: (+86) 0411-8467-5584
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  • Prof. Dr. Yonggui Robin Chi

    Corresponding author
    1. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 67911961
    • Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 67911961
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Abstract

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A proton does the two jobs: Brønsted acids alone catalyze the α-alkylation of aldehydes with diaryl alcohols. In this type of transformation, the acid-catalysis approach offers a broader substrate scope compared to the previously used enamine catalysis methods. The acid plays two important roles: one is to mediate the alcohol dehydration for carbocation formation; the other is to accelerate the rate-determining aldehyde enolization (see scheme).

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