Abstract
1,2,3-Benzodiazaboroles can be conveniently prepared from azobenzenes by a two-step protocol involving electrophilic ortho-borylation with BBr3 and dialkylative cyclization with the Grignard reagent. The methodology provides a diverse range of products equipped with functionalities from azobenzenes containing substituents (Me, t-Bu, F, Cl, Br, I, and OCF3) and a series of Grignard reagents (alkyl- and arylmagnesium reagents). Moreover, this study displays the moderate aromaticity of the B-N-N-containing five-membered ring and mechanistic investigations of the cyclization reaction.
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