Background:
In continuation of our previous work and the applications of saccharin, we encouraged
to investigate the one-pot synthesis of the aryl iodides by the diazotization of the arene diazonium saccharin
salts.
Objective:
Arene diazonium salts play an important role in organic synthesis as intermediate and a wide variety
of aromatic compounds have been prepared using them. A serious drawback of arene diazonium salts is their
instability in a dry state; therefore, they must be stored and handled carefully to avoid spontaneous explosion
and other hazard events.
Methods:
The arene diazonium saccharin salts were prepared as active intermediates in situ through the
reaction of various aryl amines with tert-butyl nitrite (TBN) in the presence of saccharin (Sac–H). Then, in situ
obtained intermediates were used into the diazotization step without separation and purification in the current
protocol.
Results:
A variety of aryl iodides were synthesized at a greener and low-cost method in the presence of TBN,
Sac–H, glacial acetic acid, and TEAI.
Conclusion:
In summary, a telescopic reaction is developed for the synthesis of aryl iodides. The current
methodology is safe, cost-effective, broad substrate scope, and metal-free. All used reagents are commercially
available and inert to moisture and air. Also, the saccharine and tetraethylammonium cation could be partially
recovered from the reaction residue, which reduces waste generation, energy consumption, raw material, and
waste disposal costs.
Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts