Issue 6, 2017

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

Abstract

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

Supplementary files

Article information

Article type
Research Article
Submitted
23 Dec 2016
Accepted
09 Feb 2017
First published
13 Feb 2017

Org. Chem. Front., 2017,4, 1069-1073

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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