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Issue 22, 2017
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Synthesis of benzil-o-carboxylate derivatives and isocoumarins through neighboring ester-participating bromocyclizations of o-alkynylbenzoates

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Abstract

Bromide mediated neighboring ester-participating bromocyclizations of o-alkynylbenzoates are described here for the synthesis of benzil-o-carboxylates. 4-bromoisocoumarins are also synthesized when phenyl o-alkynylbenzoate is used as the substrate. Mechanistic studies suggest that the whole process is composed of an electrophilic bromocyclization and a dibromohydration-based ring-opening, and the neighboring ester group participates in the bromocyclization. Interestingly, the two oxygen atoms of the keto carbonyls in benzil-o-carboxylates are both derived from water. The electrophilic bromo source is in situ generated from the oxidation of bromide.

Graphical abstract: Synthesis of benzil-o-carboxylate derivatives and isocoumarins through neighboring ester-participating bromocyclizations of o-alkynylbenzoates

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Publication details

The article was received on 05 Apr 2017, accepted on 10 May 2017 and first published on 12 May 2017


Article type: Paper
DOI: 10.1039/C7OB00845G
Citation: Org. Biomol. Chem., 2017,15, 4867-4874
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    Synthesis of benzil-o-carboxylate derivatives and isocoumarins through neighboring ester-participating bromocyclizations of o-alkynylbenzoates

    S. Yuan, H. Zhou, L. Zhang, J. Liu and G. Qiu, Org. Biomol. Chem., 2017, 15, 4867
    DOI: 10.1039/C7OB00845G

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