Development of Transition-Metal Catalyzed Carbon-Carbon Bond Forming Reactions Public Deposited
- Last Modified
- March 19, 2019
- Creator
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Lainhart, Brendan
- Affiliation: College of Arts and Sciences, Department of Chemistry
- Abstract
- Chapter One discusses our efforts towards a Rhodium-catalyzed [4 + 2 + 2] cycloaddition of diene-allenes with exogenous allenes. Our efforts began with the development of a racemic reaction achieving high yields through the use of Rh-phosphoramidite and Rh-phosphite catalyst systems. Further, we discuss the challenging development of an enantioselective variant and the methods we used to avoid the problematic [4 + 2] side reaction. We demonstrate that in these reactions, a Rh-H8-monophos complex can produce highly enantioenriched cyclooctanoid products in decent yield. The chapter finishes with a discussion of the potential reaction mechanisms and the evidence thereof. Chapter Two describes the initial efforts towards three Pd-catalyzed C-C bond forming reactions of alkyl halides: 1) The improvement of the alkyl-Heck type cyclization of alkyl iodides; 2) The development of the alkyl-Heck type cyclization of primary alkyl bromides; 3) Efforts towards the enantioselective carbonylation of alkyl iodides using both steric selectivity and directing group based selectivity.
- Date of publication
- August 2015
- Keyword
- Subject
- DOI
- Identifier
- Resource type
- Rights statement
- In Copyright
- Advisor
- Lockett, Matthew
- Meek, Simon
- Johnson, Jeffrey
- Dempsey, Jillian
- Alexanian, Erik
- Degree
- Doctor of Philosophy
- Degree granting institution
- University of North Carolina at Chapel Hill Graduate School
- Graduation year
- 2015
- Language
- Publisher
- Place of publication
- Chapel Hill, NC
- Access
- There are no restrictions to this item.
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This work has no parents.
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Lainhart_unc_0153D_15660.pdf | 2019-04-08 | Public |
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