Document Type

Honors Capstone Project

Date of Submission

Spring 5-2017

Capstone Advisor

Nancy Totah

Honors Reader

Michael Sponsler

Capstone Major

Chemistry

Capstone College

Arts and Science

Audio/Visual Component

no

Capstone Prize Winner

no

Won Capstone Funding

yes

Honors Categories

Sciences and Engineering

Subject Categories

Chemistry

Abstract

The purpose of this research is to explore the use of cobalt- and iron-catalyzed cross coupling reactions of alkyl iodides containing beta-tetrahydropyran groups to develop a general method to synthesize substituted tetrahydropyrans. Substituted tetrahydropyrans can be used towards the total syntheses of biologically active natural products. The starting iodide compounds underwent sp3-sp3 and sp3-sp2 cobalt- and iron-catalyzed cross-coupling reactions with different Grignard reagents. It was expected that the formation of the coupled product would be faster than the formation of the side products (elimination and homocoupling) and thus yield the desired substituted tetrahydropyrans. The results of this study showed that cobalt-catalyzed reactions are best used for sp3-sp3 coupling though in low yields while the iron-catalyzed reactions produced better yields for the sp3-sp2 couplings. However, the reactions still resulted in the formation of undesired elimination and homocoupling side products. In the future, optimization will be made to minimize the formation of the side products and to increase yields of the substituted tetrahydropyrans which can then provide a further basis for the use of cobalt- and iron-catalyzed cross-coupling reactions in the synthesis of natural products.

Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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Chemistry Commons

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