A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process

• Main Author: Khaligh, Nader Ghaffari
• Format: Article
• Published: Wiley 2018
• Subjects: Q Science (General); QD Chemistry
• Online Access: http://eprints.um.edu.my/21640/; https://doi.org/10.1002/hc.21418

The preparation of aryl iodides in a telescopic reaction using tert-butyl nitrite as a diazotization reagent and a mixture of bis(trifluoromethane) sulfonamide and glacial acetic acid as a mild acidic agent in ethanol followed by iododediazoniation with tetraethylammonium iodide in water was investigated. The current method has other advantages such as minimized waste by avoiding solvent for the purification of products in diazotization step, simple experimental procedure, and good yield of the sterically hindered aryl amines, metal and strong acid-free waste and environmentally benign conditions. The noteworthy features of this study are the preparation of stable arenediazonium bis(trifluoromethylsulfonyl)imide salts that can be used with no significant loss activity after 1 week and bis(trifluoromethane)sulfonamide was recovered in high yields from reactions.