Fused benzenoids and heterocycles are important classes of polyaromatic compounds derived directly from petroleum by-products such as benzene. The past four years has seen tremendous growth in metal-catalyzed and metal-free syntheses of fused ring structures including naphthalene, benzofuran, and indoles. One emerging benzannulation strategy is that of electrophilic cyclization of alkynes initiated by boron-based Lewis acids. While this metal-free approach results in the formation of fused ring systems such as benzofurans, it has yet to address the preparation of naphthalenes - fundamental aromatic moieties in the pharmaceutical and material science fields. We aim to develop a simple and facile route to borylated naphthalenes that exploits alkyne activation by boron-based Lewis acids.

Formation of trisubstituted naphthalenes: Development of a new benzannulation strategy

253rd National Meeting (2017)

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