Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

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  • Derek Yiren Ong
    Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
  • Zhihao Yen
    Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
  • Asami Yoshii
    Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
  • Julia Revillo Imbernon
    Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
  • Ryo Takita
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
  • Shunsuke Chiba
    Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
  • School of Physical and Mathematical Sciences

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<jats:title>Abstract</jats:title><jats:p>New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX<jats:sub>2</jats:sub>). Use of a different halide on ZnX<jats:sub>2</jats:sub> dictates the selectivity, wherein the NaH‐ZnI<jats:sub>2</jats:sub> system delivers alcohols and NaH‐ZnCl<jats:sub>2</jats:sub> gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH<jats:sub>2</jats:sub>)<jats:sub>∞</jats:sub> is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H−Zn−Cl)<jats:sub>2</jats:sub> is the key species for the production of amines.</jats:p>

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