Harnessing the Reactivity of ortho -Alkynylaldehydes: Silver Triflate Catalyzed Regioselective Synthesis of Phosphonylated Fluorescent Molecules.

Autor: Thakur, Deepika, Meena, Shivam A., Sushmita, Sushmita, Verma, Akhilesh K.
Předmět:
Zdroj: Synthesis; Jan2025, Vol. 57 Issue 1, p176-188, 13p
Abstrakt: 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]
Databáze: Complementary Index