Download PDF
Synthesis 2018; 50(02): 384-390
DOI: 10.1055/s-0036-1589114
paper
© Georg Thieme Verlag Stuttgart · New York

Mild, Efficient, and Regioselective Synthesis of Diiodophenyl­boronic Acid Derivatives via Metal–Iodine Exchange of 5-Substituted 1,2,3-Triiodoarenes

Raed M. Al-Zoubi*
a   Department of Chemistry, Jordan University of Science and Technology, P.O.Box 3030, Irbid, 22110, Jordan   Email: rmzoubi@just.edu.jo
,
Abdellatif Ibdah
a   Department of Chemistry, Jordan University of Science and Technology, P.O.Box 3030, Irbid, 22110, Jordan   Email: rmzoubi@just.edu.jo
,
Walid K. Al-Jammal
a   Department of Chemistry, Jordan University of Science and Technology, P.O.Box 3030, Irbid, 22110, Jordan   Email: rmzoubi@just.edu.jo
,
Mazhar S. Al-Zoubi
b   Department of Biology, Yarmouk University, P.O. Box 566, Irbid, 21163, Jordan
,
Ahmad A. Almasalma 
a   Department of Chemistry, Jordan University of Science and Technology, P.O.Box 3030, Irbid, 22110, Jordan   Email: rmzoubi@just.edu.jo
,
Robert McDonald
c   Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada
› Author AffiliationsThis work was generously funded by the Scientific Research Support Fund of Jordan (www.srf.gov.jo, Grant No. Bas/2/04/2013 for R.M.A.) and Jordan University of Science and Technology (JUST).
Further Information

Publication History

Received: 26 July 2017

Accepted after revision: 11 September 2017

Publication Date:
11 October 2017 (online)

    Permissions and Reprints All articles of this category


Abstract

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. The regio­selectivity of the reaction per se is remarkably controlled by the nature of the C5 substituent providing 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-diiodophenylboronic acid possesses 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 these compounds are difficult to prepare by other means.

Key words

1,2,3-triiodoarenes - 2,6-diiodophenylboronic acids - 2,3-diiodophenylboronic acids - metal–iodine exchange - antibacterial - antifungal

Supporting Information