Sonogashira coupling with aqueous ammonia directed to the synthesis of azotolane derivatives

Sonogashira coupling with aqueous ammonia is tolerable for the reaction of aryl iodides or terminal alkynes bearing an azobenzene group. The reaction of (4-heptyloxyphenyl)ethyne with (4-heptyloxyphenyl)-(4-iodophenyl)diazene in the presence of 1 mol% of PdCl2(PPh3)(2), 2 mol% of CuI, and 2 equiv of 0.5 M aqueous ammonia gives the corresponding azotolane in 87% isolated yield after stirring at room temperature for 15 h. (C) 2004 Elsevier Ltd. All rights reserved.