Aryl halides possess synthetic properties that make them important intermediates in multiple reactions. In the pharmaceutical industry, Kimishima and their research team developed oxycodone through direct arylation of aryl bromides. In addition, the Ullmann-Goldberg reaction utilizes copper in conjunction with aryl halides to produce new C-X bonds (X = C, O, N). Furthermore, aryl bromides are common reactants in metal mediated cross-coupling reactions, such as the Nobel Prize winning Suzuki-Murayama reaction of aryl halides and boronic acids. As such, aryl halides are proven to be versatile synthetic intermediates in fields including natural project synthesis, as well as the pharmaceutical and material science industries. Therefore, new methods of preparing aryl halides will be valuable tools to synthetic chemists. Our group is interested in producing aryl halides through dialkyl triazene decomposition. First, we report the synthesis of several dialkyl triazene derivatives, followed by the subsequent decomposition of these compounds in the presence of boron trihalides.

Synthesis of aryl halides by triazene decomposition

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