Arene diazonium saccharin intermediates: a greener and cost-effective alternative method for the preparation of aryl iodide

Lia Zaharani,Mohd Rafie Johan,Zohreh Shahnavaz,Nader Ghaffari Khaligh

doi:10.3906/kim-2002-26

Abstract

In the current protocol, the arene diazonium saccharin derivatives were initially produced from various substituted aromatic amines; subsequently, these intermediates were treated with a greener organic iodide for the preparation of the aryl iodide. We tried to choose low-cost, commercially available, biodegradable, recoverable, ecofriendly, and safe reagents and solvents. The arene diazonium saccharin intermediates could be stored in the liquid phase into a refrigerator for a long time with no significant loss activity. The outstanding merits of the current protocol (a) included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reaction steps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates, and (d) avoid the generation of heavy metal or corrosive waste.

Highlights

In the course of our research regarding the synthesis of aromatic iodides through the Sandmeyer reaction or its alternatives, we required an efficient, low cost, and sustainable method for accessing relative stable arene diazonium salts
In continuation of our previous work [4] and application of saccharin [5,6,7], we encouraged to investigate the potential of saccharin for the synthesis of the aryl iodides through in situ formation the arene diazonium saccharin salts which to the best of our knowledge has not been presented to date
According to the current strategy, aryl iodides are formed from diazotization of in situ generated arene diazonium salts which are in turn formed from aniline derivatives and tert-butyl nitrite (TBN) in the presence of saccharin

Summary

Introduction

In the course of our research regarding the synthesis of aromatic iodides through the Sandmeyer reaction or its alternatives, we required an efficient, low cost, and sustainable method for accessing relative stable arene diazonium salts. It is clear that the anion nature can influence in situ the generation of the arene diazonium salts [2], and facilitated the preparation of aryl iodides. In continuation of our previous work [4] and application of saccharin [5,6,7], we encouraged to investigate the potential of saccharin for the synthesis of the aryl iodides through in situ formation the arene diazonium saccharin salts which to the best of our knowledge has not been presented to date.

Results

Conclusion