KO(t)Bu/DMSO-promoted C-H functionalization of acetylarenes with arylacetylenes (100 °C, 30 min), generating β,γ-ethylenic ketones, triggers upon further heating (100 °C, 4 h, with or without acidifying additive) the cascade assembly of acyl terphenyls and higher polyaromatics in good yields.

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An unprecedented self-organization of three molecules of acetylene, two molecules of o-halo arylamine, and one molecule of water to 1-acetyl-1,3-bis­(haloarylamines) in the KOH/DMSO system has been discovered. These high-value 1,3-bis­(arylamines) are capable of acting as efficient “platform molecules” to provide one-pot access to hexahydropyrrolo­[3,2-b]­indoles, 3-haloarylamino-pyrrolidines, benzyliden piperidinols, and other functionalized diamines.

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