Dialkyltriazenes have been useful starting materials for heterocycle synthesis and the production of arylamines and iodoarenes. Due to their robust and inert nature towards palladium cross-coupling reaction conditions, dialkyltriazenes have utility as masking groups for iodoarenes in the discrete syntheses of phenylacetylene macrocycles. More specifically, dialkyltriazenes undergo decomposition under a wide variety of reaction conditions – most notably with MeI to yield trialkyl amines, N<sub>2</sub>, and iodoarenes. This reaction and other routes leading to iodoarenes are well established, the production of bromoarenes from trizanes are limited. We therefore, have established a new method for dialkyltriazene decomposition, mediated by boron tribromide, which leads to bromoarenes in high yields.

Dialkyltriazene decomposition leading to bromoarenes: A boron tribromide-mediated process

253rd National Meeting (2017)

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