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Synthesis 2020; 52(09): 1369-1378
DOI: 10.1055/s-0039-1690838
DOI: 10.1055/s-0039-1690838
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Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride
This work was supported by funding from Nanyang Technological University (NTU) and the Ministry of Education - Singapore (Academic Research Fund Tier 1: RG10/17).Further Information
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690838.
- Supporting Information
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For lithium or sodium tris(dialkylamino)aluminum hydrides [M(R2N)3AlH; M = Li or Na], see:
For lithium diisobutylmorpholinoaluminum hydride and its derivatives, see: