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An efficient approach for the facile synthesis of phosphonylated 1,3-dihydrofuro[3,4- b ]quinolines and dihydrofuro[3,4- b ]pyridines is developed. Reaction proceeds by the formation of new C–P and C–O bonds affording Z -selective phosphonylated products at room temperature. Diphenylphosphine oxides and dialkyl phosphites are explicitly incorporated into the carbonyl carbon of o -alkynylaldehydes in good to excellent yields. The reaction exhibits mild conditions, broad substrate scope, and the formation of three new bonds in the presence of a silver catalyst. The mechanistic studies revealed that the reaction proceeded via an ionic pathway in a 5- exo -dig manner to give Z -selective products, which was validated by X-ray crystallographic studies. Photophysical studies of selected compounds revealed the emission maxima in the range of 455 nm. [ABSTRACT FROM AUTHOR]