Organic Letters 2007-07-05

Efficient nucleophilic aromatic substitution between aryl nitrofluorides and alkynes.

Patrick L DeRoy, Simon Surprenant, Megan Bertrand-Laperle, Christiane Yoakim

Index: Org. Lett. 9(14) , 2741-3, (2007)

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Abstract

The nucleophilic aromatic substitution reaction between electron-deficient aryl fluorides and terminal alkynes is shown to be efficiently promoted by sodium bis(trimethylsilyl)amide as a base. Moderate to excellent yields of 2-ethynylnitrobenzene products can be obtained under mild conditions.