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Issue 6, 2017
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KBr/K2S2O8-mediated dibromohydration of N-(2-alkynylaryl)acetamide

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The regioselective dibromohydration of N-(2-alkynylaryl)acetamide with the participation of a neighbouring acetamino group is described here for the synthesis of N-(2-(2,2-dibromo-2-arylacetyl)aryl)acetamide. The dibromohydration proceeds under mild conditions and works well without metal catalysis. More importantly, by employing different neighbouring groups, switchable synthesis can be achieved. The entire process of the dibromohydration of N-(2-alkynylaryl)acetamide consists of KBr/K2S2O8-based electrophilic 6-exo cyclization to form bromo-containing benzoxazine cation and the oxidative ring-opening of the resulting bromo-containing benzoxazine cation. Water serves as a reagent to be incorporated into the acetamino group.

Graphical abstract: KBr/K2S2O8-mediated dibromohydration of N-(2-alkynylaryl)acetamide

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The article was received on 23 Dec 2016, accepted on 09 Feb 2017 and first published on 13 Feb 2017

Article type: Research Article
DOI: 10.1039/C6QO00840B
Citation: Org. Chem. Front., 2017,4, 1069-1073
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    KBr/K2S2O8-mediated dibromohydration of N-(2-alkynylaryl)acetamide

    G. Qiu, Y. Li, L. Ma and H. Zhou, Org. Chem. Front., 2017, 4, 1069
    DOI: 10.1039/C6QO00840B

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