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A Mild Synthetic Protocol for Conversion of Aldehydes to Nitriles Using a Copper Catalyst and LiHMDS as the Nitrogen
Joakim Bøgelund Jakobsen1, Xinkai Wu1, Markus Staudt1
1Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, 2100 Copenhagen, Denmark.
None:
Interconversion of functional groups in organic chemistry is a key task. Here we have developed an oxidative transformation of aldehydes to nitriles using lithium bis(trimethylsilyl)amide as a nitrogen source and copper iodide as an inexpensive catalyst under aerobic and ligand free conditions. The reaction proceeds in 23-98% yield (median of 78%), tolerating various functional groups (22 examples). Furthermore, the reaction was easily scaled to 25 mmol (3.2 g of nitrile product), potentially making it relevant for industry applications.
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