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Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride

Derek Yiren Ong, Shunsuke Chiba*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: Shunsukentu.edu.sg

D. Y. Ong, S. Chiba, Synthesis, 2020, 52, 1369-1378.

DOI: 10.1055/s-0039-1690838 (free Supporting Information)


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Abstract

The combination of sodium hydride and zinc chloride enables a controlled reduction of nitriles to aldehydes via iminyl zinc intermediates. An in situ reaction of intermediates derived from aromatic nitriles with allylmetal nucleophiles affords homoallylamines. The method allows the reduction of aliphatic and aromatic nitriles under milder reaction conditions with wide functional group compatibility.


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Key Words

reduction of nitriles, hydrolysis, sodium hydride, zinc chloride


ID: J66-Y2020