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Synfacts 2009(8): 0904-0904  
DOI: 10.1055/s-0029-1217483
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

MIDA Boronates: A New Stable Form of Boronic Acids for Coupling Reactions

Contributor(s): Paul Knochel, Andrei Gavryushin
D. M. Knapp, E. P. Gillis, M. D. Burke*
University of Illinois at Urbana-Champaign, USA
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Publikationsdatum:
23. Juli 2009 (online)

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Significance

Many of potentially useful boronic acids, especially heterocyclic derivatives, are inherently unstable, what strongly limits their synthetic utility. The new N-methyliminodiacetic acid (MIDA) boronates described herein are well suitable for long-term storage, and at the same time they can be directly coupled with aryl halides due to the controlled hydrolysis under the conditions of the Suzuki reaction.