Regioselective radical arylation: silver-mediated synthesis of 3-phosphorylated coumarins, quinolin-2(1H)-one and benzophosphole oxides?

Organic & Biomolecular Chemistry Pub Date: 2019-08-13 DOI: 10.1039/C9OB01585J

Abstract

A silver-mediated domino radical addition/cyclization reaction of diarylphosphine oxides with propynoic acid derivatives is described in this article. The reaction of diarylphosphine oxides with alkynoates or propynoic amide was regioselective, producing 3-phosphorylated coumarins and benzophosphole oxides in moderate to good isolated yield, respectively. The hydrogen bond between P[double bond, length as m-dash]O and N–H was proposed to assist the vinyl radical regioselective arylation process. The reaction conditions were also compatible with the conversion of dialkylphosphine oxides to 3-phosphorylated-coumarins and quinolin-2(1H)-one in good yields.

Graphical abstract: Regioselective radical arylation: silver-mediated synthesis of 3-phosphorylated coumarins, quinolin-2(1H)-one and benzophosphole oxides
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