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Rh(III)-Catalyzed Halogenation of Vinylic C-H Bonds: Rapid and General Access to Z-Halo Acrylamides

Nadine Kuhl, Nils Schröder and Frank Glorius*

*Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany, Email: gloriusuni-muenster.de

N. Kuhl, N. Schröder, F. Glorius, Org. Lett., 2013, 15, 3860-3863.

DOI: 10.1021/ol4015915 (free Supporting Information)


Abstract

A regio- and stereoselective iodination, along with some examples for bromination, of readily available acrylamides proceeds under mild conditions via a Rh(III)-catalyzed C-H-activation/halogenation mechanism.  The reaction represents a rare example of a direct halogenation of electron-poor acrylic acid derivatives to access a variety of differently substituted Z-haloacrylic acid derivatives.

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Key Words

iodination, bromination, NIS, NBS


ID: J54-Y2013