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 react...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2005-03, Vol.2005 (6), p.1044-1051
Main Authors: Yoo, Woo-Jin, Tsui, Gavin C., Tam, William
Format: Article
Language:English
Subjects:
Boronic acids
Norbornadienes
Palladium/ Catalysis
Suzuki couplings
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Summary: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400713