Tuesday, 24 May 2005

This presentation is part of: Graduate Posters

Protodeboronation investigation in Heterogenously catalyzed Suzuki-Miyaura cross-coupling reaction

Lubabalo T. Bululu and Dr. John R. Sowa. Seton Hall University, South Orange, NJ

<>Protodeboronation Investigation in Heterogenously catalyzed Suzuki Cross-Coupling reaction. <>                          

            The high reactivity towards activation of C-X bond in aryl halides has earmarked the heterogenous Pd catalyst as a useful catalyst for suturing new c-c bonds in the Suzuki-Miyaura reaction (scheme 1, pathway A).  Unfortunately, in some cases, the catalyst is not as selective as it is anticipated.  For example, the reaction can follow 3 separate pathways: A, B, and C (scheme 1).  Of course, these pathways have different rates, usually in this following order: A > B >>> C.  Protodeboronation, B, is typically the competitive side reaction to the desired pathway A.   

Although the cause of protodeboronation is known, the mechanism is still obscure.  We intend to investigate how this process occurs.  That is, we examine how the metal center, solvent ratio, base, and substitution effects on the boronic acid, influence protodeboronation.  Lastly, we would like to isolate the source of the proton since there are potentially three different donors i.e. 1, ethanol, and water.




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