Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation

Fabien Emmetiere; Alexander J. Grenning

doi:10.1055/s-0040-1707184

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(20): 3077-3085
DOI: 10.1055/s-0040-1707184

paper

Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation

Fabien Emmetiere

,

Alexander J. Grenning ∗

Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL 32611-7200, USA eMail: grenning@ufl.edu

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Abstract

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Abstract

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.

Key words

Knoevenagel adducts - malononitriles - oxidative decyanation - redox processes - terpenoid synthesis

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