Anti-Markovnikov Functionalization of Olefins: Rhodium-Catalyzed Oxidative Aminations of Styrenes

Authors


  • Anti-Markovnikov Functionalization of Unsaturated Compounds, Part 1. We thank Degussa AG, Heraeus AG, and Hoechst AF for gifts of chemicals. We also thank Dr. J. Herwig, Dr. H. Geissler, Dr. R. Fischer, and Prof. Dr. K. Kühlein (all from the Hoeschst AG, Frankfurt) for suggestions and discussions. Harald Trauthwein thanks the Fonds der Chemischen Industrie for a doctoral scholarship.

Abstract

original image

Not the Markovnikov product 4, but the anti-Markovnikov product 3 is obtained by the oxidative amination of styrenes 1 with secondary amines 2. The oxidant in this rhodium-catalyzed reaction is the olefin itself, which is reduced to the ethylarene 5. Ar = aryl, R = alkyl, aryl.

Ancillary