Antiaromaticity in conjugated systems has long stimulated experimental and theoretical interest. Conjugated systems with fused aromatic benzenoid and antiaromatic cyclobutadienoid units are intriguing targets for the study of antiaromaticity and its potential applications. However, their syntheses have been challenging and limited. We developed an efficient and versatile strategy to synthesize a large variety of polycyclic conjugated hydrocarbons (PCHs) containing antiaromatic cyclobutadienoids. The synthesis was achieved through efficient palladium-catalyzed annulation of aryl bromides and oxanorbornenes, both of which are readily available building blocks, followed by aromatization under acidic conditions. Experimental and computational studies support the presence of antiaromaticity and its perturbation of adjacent aromaticity.

Polycyclic conjugated hydrocarbons containing antiaromatic cyclobutadienoids enabled by efficient annulation

254th National Meeting (2017)

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