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Functional Group Interconversion Of Alkylidenemalononitriles To Primary Alcohols By A Cooperative Redox Operation

Alexander J. Grenning, Fabien Emmetiere

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Functional group interconversions are essential chemical processes enabling synthesis. In this report, we describe a strategy to convert alkylidenemalononitriles into primary alcohols in one step. The reaction relies on a choreographed redox process involving alkylidene reduction, malononitrile oxidation, and acylcyanide reduction where molecular oxygen and NaBH4 work cooperatively. The method was applied to a variety of carbon skeletons and was utilized to synthesize complex terpenoid architectures.