Synthesis 2020; 52(09): 1369-1378
DOI: 10.1055/s-0039-1690838
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© Georg Thieme Verlag Stuttgart · New York

Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride

Derek Yiren Ong
,
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Email: Shunsuke@ntu.edu.sg
› Author Affiliations
This work was supported by funding from Nanyang Technological University (NTU) and the Ministry of Education - Singapore (Academic Research Fund Tier 1: RG10/17).
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Publication History

Received: 23 December 2019

Accepted: 04 February 2020

Publication Date:
19 February 2020 (online)


Abstract

A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.

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