A Mild and Versatile Method for Palladium‐Catalyzed Cross‐Coupling of Aryl Halides in Water and Surfactants

Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università degli Studi dell’Aquila, Via Vetoio − Coppito due, 67010 L’Aquila, Italy, Fax: (internat.) + 39-0862/433753
European Journal of Organic Chemistry (Impact Factor: 3.15). 02/2004; 2003(20):4080 - 4086. DOI: 10.1002/ejoc.200300356

ABSTRACT Various aqueous surfactants proved to be excellent media for carrying out palladium-catalyzed Suzuki−Miyaura cross-coupling reactions under mild conditions. The dehalogenation side reaction, which is usually a drawback with the aqueous protocol, was not observed. The concentration of the surfactant in water played a pivotal role for the reaction outcome. Smooth cross-coupling of iodoanisole and a variety of aryl bromides, including electron-rich derivatives, with aryl boronic acids occurred at room temperature in high yields either with [Pd(PPh3)4] or Pd/C as catalyst. The water-surfactant Pd/C system combines high activity under ambient conditions (air), easy separation and recyclability. Palladium acetate was found to be effective in cross-coupling of the less reactive aryl chlorides at 100 °C. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)