The Sonogashira coupling of 2-ethynyl, 4-ethynyl and 2,7-diethynyl derivatives of 1,8-bis(dimethylamino)naphthalene (proton sponge) with 1-iodo- and 1,8-diiodonaphthalenes has been studied. The reaction of the above alkynes with 1-iodonaphthalene gave the expected naphthylethynyl derivatives of proton sponge. At the same time, the coupling of 2-ethynyl- and 2,7-diethynyl-1,8-bis(dimethylamino)naphthalenes with 1,8-diiodonaphthalene resulted in the formation of N,N,7-trimethyl-7H-acenaphtho[1,2-b]benzo[g]indol-8-amines. The reaction of 1,8-diiodonaphthalene with 4-ethynyl-1,8-bis(dimethylamino)naphthalene produced 14-(4,5-bis(dimethylamino)naphthalen-1-yl)-N¹¹,N¹¹,N¹²,N¹²-tetramethylnaphtho[1,2-k]fluoranthene-11,12-diamine together with 4-((8-iodonaphthalen-1-yl)ethynyl)-N¹,N¹,N⁸,N⁸-tetramethylnaphthalene-1,8-diamine. It was suggested that the mechanisms of the two novel cascade transformations stem from the specific nature of the proton sponge substrates.

研究了1,8-双（二​​甲基氨基）萘（质子海绵）的2-乙炔基，4-乙炔基和2,7-二乙炔基衍生物与1-碘-和1,8-二碘代萘的Sonogashira偶联。上述炔烃与1-碘萘的反应得到了质子海绵的预期的萘乙炔基衍生物。同时，2-乙炔基和2,7-二乙炔基-1,8-双（二​​甲基氨基）萘与1,8-二碘萘的偶合导致N，N，7-三甲基-7 H-的形成。 ena [1,2- b ]苯并[ g ]吲哚-8-胺。1,8-二碘萘与4-乙炔基-1,8-双（二​​甲基氨基）萘反应生成14-（4,5-双（二甲基氨基）萘-1-基）-N ¹¹，N ¹¹，N ¹²，N ^12-四甲基萘[1,2 - k ]荧蒽-11,12-二胺与4-（（8-碘萘基-1-基）乙炔基）-N ¹，N ¹，N ⁸，N ^8-四甲基萘-1,8-二胺。有人认为，这两个新的级联转化的机制是基于质子海绵底物的特殊性质。