A Simple and Efficient Two-Step Synthesis of 1,2,3-Triiodoarenes via Consecutive C–H Iodination/ipso-Iododecarboxylation Strategy: A Potential Application towards ortho-Diiodoarenes by Regioselective Metal–Iodine Exchange Reaction
Raed M. Al-Zoubi A C , Hussein Al-Mughaid A and Robert McDonald B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Jordan University of Science and Technology, P.O. Box 3030, Irbid, 22110, Jordan.
B Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Alberta, T6G2G2, Canada.
C Corresponding author. Email: rmzoubi@just.edu.jo
Australian Journal of Chemistry 68(6) 912-918 https://doi.org/10.1071/CH14386
Submitted: 14 June 2014 Accepted: 1 September 2014 Published: 18 November 2014
Abstract
A general, robust, and efficient method for the conversion of benzoic acids to 1,2,3-triiodoarenes and 1,2,3-trihaloarenes via a two-step synthesis is reported. Commercially available benzoic acids were used that can allow the reactions to be performed on multi-gram scales with good-to-excellent yields. This report discloses a practical method for the synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, scalable, and easy to workup and purify. A potential application of the target compounds as precursors for novel regioselective metal–iodine exchange reaction of 1,2,3-triiodoarenes was also demonstrated. It provided ortho-diiodoaryl derivatives in a high regioselective fashion that are useful intermediates in synthesis and indeed are hard to synthesize by any other means.
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