Palladium‐Catalyzed Suzuki Couplings of 2,3‐Dibromonorbornadiene: Synthesis of Symmetrical and Unsymmetrical Aryl‐Substituted Norbornadienes

Palladium-catalyzed Suzuki coupling reactions between 2,3-dibromonorbornadiene and arylboronic acids were investigated. These reactions provide an efficient method for the synthesis of symmetrical 2,3-diarylnorbornadienes which are not accessible using the traditional Diels–Alder cycloaddition reactions. The optimized reaction conditions of the Suzuki coupling reactions were found using [Pd2(dba)3] (0.5 mol%), tBu3P (1.4 mol%) and CsF in THF. High yields of the Suzuki coupling products were obtained when electron-rich arylboronic acids were used. On the other hand, Suzuki coupling reactions with electronic-deficient or sterically hindered arylboronic acids gave lower yields of the corresponding 2,3-di-arylnorbornadienes. Unsymmetrical mono- and diaryl-substituted norbornadienes were also prepared in good yields using this method. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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