Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 4, Pages 2654-2665Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02705
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- Japan Society for the Promotion of Science [171, 05794]
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Nickel-catalyzed transformation of alkenete-thered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.
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