Return to search

Mechanism of the Heck reaction: nature of oxidative addition and migratory insertion

The mechanism of carbon coupling reactions is traditionally represented in a very broad schematic. This thesis seeks to explore the mechanism of these reactions by focusing on Heck olefination. The Heck reaction has become a powerful tool in synthetic labs but the mechanism of this reaction has remained a topic of debate since the reaction's discovery. The catalytic cycle that has come to be accepted, while accurate in its own right, is not nearly as detailed as the complexity of the various stages of the Heck reaction suggest it should be. This study seeks to elucidate the nature of the oxidative addition of aryl halide to a palladium catalyst using a ligand that has been shown to have high activity in facilitating oxidative addition of aryl chlorides and bromides in other coupling reactions. This information is then compared to other studies in the field so that conclusions can be drawn about the oxidative addition. Also, selectivity studies seek to determine the nature of the migratory insertion of an olefin into the Pd-Ar bond. Again, comparison of results obtained in this study are compared to previous results so that a more definitive conclusion can be drawn about the oxidative addition.

Identiferoai:union.ndltd.org:TEXASAandM/oai:repository.tamu.edu:1969.1/1130
Date15 November 2004
CreatorsEvans, Anthony Steven
ContributorsSingleton, Daniel, Ford, David, Miller, Stephen A.
PublisherTexas A&M University
Source SetsTexas A and M University
Languageen_US
Detected LanguageEnglish
TypeElectronic Thesis, text
Format416963 bytes, 95488 bytes, electronic, application/pdf, text/plain, born digital

Page generated in 0.0021 seconds