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

Dedicated in Honor of Prof. H. Ila

Abstract

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.

Key words

diphenylphosphine oxide - o-alkynylaldehydes - 1,3-dihydrofuro[3,4-b]quinolines - alkynes - phosphonylated

Publication History

Received: 22 May 2024

Accepted after revision: 27 June 2024

Accepted Manuscript online:
28 June 2024

Article published online:
22 July 2024

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