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Regioselective Radical Arylation: Silver-Mediated Synthesis of 3-Phosphorylated-Coumarins, Quinolin-2(1H)-one and Benzophosphole Oxides

Abstract

A silver-mediated domino radical addition/cyclization reaction of diarylphosphine oxides with propynoic acid derivatives were described. The reaction products of diarylphosphine oxides with alkynoates or propynoic amide in different regioselectivities, giving 3-phosphorylated coumarins and benzophosphole oxides in moderate to good isolated yields, respectively. The hydrogen bond between the P=O and NH was proposed to assist the vinyl radical regioselective arylation process. Dialkylphosphine oxides also compatible, and gave the 3-phosphorylated-coumarins and quinolin-2(1H)-one in good yields.

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Publication details

The article was received on 17 Jul 2019, accepted on 13 Aug 2019 and first published on 13 Aug 2019


Article type: Paper
DOI: 10.1039/C9OB01585J
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Regioselective Radical Arylation: Silver-Mediated Synthesis of 3-Phosphorylated-Coumarins, Quinolin-2(1H)-one and Benzophosphole Oxides

    H. Hou, Y. Xu, H. Yang, C. Yan, Y. Shi and S. ZHU, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB01585J

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