Grignard reagents react with diisopropylaminoborane, BH2N(iPr)2, at ambient reaction conditions yielding the corresponding boronic acid.  This reaction is general and can accommodate aliphatic, aromatic, and heteroaromatic halides.  One equivalent of Grignard reacts with one equivalent of BH2N(iPr)2 in THF, the reaction is complete within one hour affording the product in good to excellent yield. Boronic acids can also be produced under Barbier-type conditions. An array of simple alkyl and aryl substrates were synthesized by this method.

Facile synthesis of alkyl, aryl, heteroaryl boronic acids: Reaction of diisopropylaminoborane with corresponding halides mediated by magnesium under ambient Grignard and Barbier conditions

243rd National Meeting (2012)

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