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 1mol% of PdCl2 (PPh3) 2, 2mol% of CuI, and 2equiv of 0.5 M aqueous ammonia gives the corresponding azotolane in 87% isolated yield after stirring at room temperature for 15h.
