Functional group concentrated arenes are prevalent key building blocks which are frequently found in pharmaceuticals, materials and other bioactive compound. Traditional synthetic methods require lengthy multi-step procedures involving sequential functional group installation and interconvertion, which leaves considerable room for improvement in this field. Consequently, the past more than ten years witnesses the significant progress in the development of efficient methods for functionalization of abundant cyclohexanones via dehydrogenative desaturation of saturated reactants to the corresponding unsaturated intermediates, which not only expands the reactivity repertoire of these carbonyl compounds but also provides a concise approach to streamlined syntheses of complex functionalized compounds starting from readily available reactants. Herein, we report the tandem dehydrogenation-driven cross-coupling reactions between cyclohexanones and primary amines for multi-functionalized arene syntheses by TEMPO’s multiple reactivity modes (oxygenation and desaturation). These protocols features broad substrate scope, high functional group tolerance and easy operation, therefore enables late-stage functionalization and rapid synthesis of bioactive compounds including structurally complex marketed drugs and natural products.

Transformation of cyclohexanones via enamine mediated dehydrogenative multi-functionalization

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