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Arylboronic Acids in Self-condensation of Glucosamines Forming Deoxyfructosazine, Catalysts or Reagents?

preprint
revised on 05.05.2019 and posted on 06.05.2019 by Meifeng Wang, Gan Zhu, Yiqun Li, Liuqun Gu
Arylboronic acids were widely used as efficient catalysts in direct amide formation and other organic transformations. Surprisingly, reports on their use as catalysts in carbohydrates synthesis are very rare even though boron acid-diol complexation was extensively investigated in molecular recognition for saccharides and so on. Here we developed an efficient arylboronic acids catalyzed dimerization of glucosamines forming deoxyfructosazine which is important compound in pharmaceutical and food industries, against a commonly held belief that excess amount of phenyl boronic acid (or boric acid) is a must. A catalytic mechanism was also proposed and arylboronic acids instead of their boronates was identified as catalysts.

Funding

National Natural Science Foundation of China (No. 21372099)

startup funding from Jinan University to L. Gu (No: 88015155 and 88016607)

History

Email Address of Submitting Author

guliuqun@yahoo.com

Institution

Jinan University

Country

China

ORCID For Submitting Author

0000-0002-4254-6824

Declaration of Conflict of Interest

no conflict of interest

Version Notes

Version 3 with significant changes based on reviewers'comments.

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