Raed M. Al-Zoubi
Jordan University of Science and Technology, Jordan
Title: Mild, Efficient and Regioselective Synthesis of Diiodophenyl boronic Acid Derivatives via Metal-Iodine Exchange of 5-Substituted-1,2,3-Triiodoarenes
Biography
Biography: Raed M. Al-Zoubi
Abstract
A unique 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives have been synthesized via regioselective Metal-Iodine Exchange (MIE) of 5-substituted 1,2,3-triiodoarenes is reported. The regioselectivity of the reaction per se is remarkably controlled by the nature of C-5 substituent providing either the desired diiodophenylboronic acids in moderate to good yields and with high site-selectivity. The diiodophenylboronic acids were then examined for in-vitro antimicrobial activity against four strains of bacteria Micrococcus luteus (ATCC 9341), Bacillus Cereus (ATCC 11778), Escherichia coli (ATCC 25922) and Serratia marcescens (ATCC 27117) and one fungal strain Candida albicans using well diffusion assay and dilution method. It indicated that (5-fluoro-2,3-diiodophenyl)boronic acid (compound 16B) possess the most potent antibacterial and antifungal activity with MIC of 2.6 mg/mL for M. luteus and C. albicans. This report discloses a one-step protocol to access hitherto unknowns 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives that is scalable, good in scope, no chromatography is needed and indeed difficult to be prepared by other means.
Recent Publications (minimum 5)
[1] a) M. Bérubé, M. Dowlut and D. G. Hall, J. Org. Chem. 2008, 73, 6471-6479; b) W. Yang, X. Gao and B. Wang, Med. Res. Rev. 2003, 23, 346-368.
[2] a) R. M. Al-Zoubi and D. G. Hall, Org. Lett. 2010, 12, 2480-2483; b) R. M. Al-Zoubi, O. Marion and D. G. Hall, Angew. Chem. Int. Ed. 2008, 47, 2876-2879; c) N. Gernigon, R. M. Al-Zoubi and D. G. Hall, J. Org. Chem. 2012, 77, 8386-8400; d) T. Marcelli, Angew. Chem. Int. Ed. 2010, 49, 6840-6843.
[3] T. J. Zimmermann, M. Buerger, E. Tashiro, Y. Kondoh, N. E. Martinez, K. Goermer, S. Rosin-Steiner, T. Shimizu, S. Ozaki, K. Mikoshiba, N. Watanabe, D. Hall, I. R. Vetter, H. Osada, C. Hedberg and H. Waldmann, ChemBioChem 2013, 14, 115-122.
[4] T. Akama, K. Jarnagin, J. J. Plattner, S. R. Pulley, W. H. White, Y.-K. Zhang and Y. Zhou, Eli Lilly & Anacor Pharmaceuticals Inc. World patent WO2014149793A1, 2014, p. 160.