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Vibrational Spectroscopy of N-methyliminodiacetic Acid (MIDA)-protected Boronate Ester: Examination of the B-N Dative Bond

Vibrational Spectroscopy of N-methyliminodiacetic Acid (MIDA)-protected Boronate Ester: Examination of the B-N Dative Bond

Dana N Reinemann, Ashley M Wright, Jonathan D Wolfe, Gregory S Tschumper, Nathan I Hammer

J Phys Chem A. 2011 Jun 23;115(24):6426-31.

PMID: 21557585

Abstract:

N-methyliminodiacetic acid (MIDA)-protected boronate esters are a new class of reagents that offer great promise in iterative Suzuki-Miyaura cross-coupling reactions. Compared to earlier reagents, MIDA esters are easily handled and are benchtop stable under air indefinitely. The success of this new species is tied to its unique molecular architecture. Compared to the simpler B-N containing molecules ammonia borane and trimethylamine borane, MIDA esters are much larger, and the sp(3) hybridized boron atom is secured by two five membered rings, making this molecular class stable for spectroscopic study. Here, we present infrared, Raman, and surface enhanced Raman (SERS) spectra of methylboronic acid MIDA ester. Comparisons of the spectroscopic results to those from electronic structure calculations suggest that the B-N stretching mode in this molecule lies in the range 560-650 cm(-1), making it among the lowest energy vibrations observed to date that can be primarily attributed to B-N stretching.

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