Hydroxylated (hetero)aromatic groups are common structural elements found in high value molecules such as bioactive natural products, pharmaceuticals, agrochemicals, conducting polymers, and organic dyes. These compounds also serve as building blocks for more complex synthesis. Given this diverse utility, the development of methods to access these scaffolds has been an important goal for synthetic chemists.  In this study, we present a Lewis acid-catalyzed homo-Nazarov-type intramolecular ring-opening cyclization of alkylidene cyclopropanes (ACPs) to provide a variety of hydroxylated aromatic and heteroaromatic scaffolds. The method allows for the synthesis of substituted phenols, naphthols, benzofurans, indoles and carbazoles in yields up to 91%.

Catalytic, formal homo-Nazarov-type cyclizations of alkylidene cyclopropanes: Access to hydroxylated (hetero)aromatics

248th National Meeting (2014)

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