Efficient Preparation of 2-Aminomethylbiphenyls via Suzuki-Miyaura Reactions

Abstract

We prepared four 2-(aminomethyl)arylboronic acids and studied their reactivity in the Suzuki-Miyaura coupling reaction with different aryl halides. We observed significant increases in yields and shorter reaction times when the amine adjacent to the boronic acid was protected by a tert-butyloxycarbonyl (t-Boc) group. We then investigated the origin of the greater reactivity of N-t-Boc-protected substrates with regard to the potential role of an N-B bond.

Suzuki-Miyaura cross-coupling - biaryls - (aminomethyl)arylboronic acids - N-B dative bond

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