palladium-catalyzed heck coupling reaction of aryl bromides in aqueous media using tetrahydropyrimidinium salts as carbene ligands钯催化的见鬼偶联芳基溴化物的反应在水媒体使用tetrahydropyrimidinium盐作为碳烯配体.pdf

Molecules 2010, 15, 649-659; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Palladium-Catalyzed Heck Coupling Reaction of Aryl Bromides in Aqueous Media Using Tetrahydropyrimidinium Salts as Carbene Ligands Sedat Yaşar 1, Emine Özge Özcan 2, Nevin Gürbüz 2, Bekir Çetinkaya 3 and İsmail Özdemir 2,* 1 Department of Chemistry, Faculty of Science and Art, Gaziosmanpaşa University, 60240 Tokat, Turkey; E-Mail: syasar44@ (S.Y.) 2 Department of Chemistry, Faculty of Science and Art, İnönü University, 44280 Malatya, Turkey; E-Mails: eozgeozcan@ (E.Ö.Ö.); ngurbuz@.tr (N.G.) 3 Department of Chemistry, Faculty of Science, Ege University, 35100 İzmir, Turkey; E-Mail: bekircetinkaya@.tr (B.C.) * Author to whom correspondence should be addressed; E-Mail: iozdemir@.tr; Tel.: +904223410212; Fax: +904223410212. Received: 16 December 2009; in revised form: 1 January 2010 / Accepted: 12 January 2010 / Published: 28 January 2010 Abstract: An efficient and stereoselective catalytic system for the Heck cross coupling reaction using novel 1,3-dialkyl-3,4,5,6-tetrahydropyrimidinium salts (1, LHX) and Pd(OAc)2 loading has been reported. The palladium complexes derived from the salts 1a-f prepared in situ exhibit good catalytic activity in the Heck coupling reaction of aryl bromides under mild conditions. Keywords: carbene; C-C coupling; palladium/tetrahydropyrimidinium; Heck coupling 1. Introduction The Heck reaction, one of the mo