Microwave-irradiated benzoylation reactions and coupling reactions

Maya Chen Wai, Tennessee State University

Abstract

In this thesis paper, three new procedures for benzoylation reactions were developed using microwave heating. Benzoylation is an important organic transformation and has many applications for developing cyclooxygenase (COX) inhibitors like non-steroidal anti-inflammatory drugs (NSAIDs). The procedures that were developed are based on literature review of other research groups and the previous work and successes of former graduate students. One of the procedures that was developed is C-benzoylation utilizing a Lewis acid catalyst, aluminum chloride, in a solvent-free system. Another procedure that was developed is solvent-free, N-benzoylation without the aid of any catalyst. These C-benzoylation and N-benzoylation procedures are solvent-free and therefore, more environmentally friendly. Finally palladium-catalyzed cross-coupling reactions between potassium phenyltrifluoroborates and benzoyl chlorides were explored for optimal conditions. All these reactions utilize microwave irradiation to maximize transformation, obtain high yield, and have reduced reaction time compared to conventional heating methods. Successful C-benzoylation and N-benzoylation transformations were reported with the percent yields in the results tables. The products were analyzed and confirmed by gas chromatography - mass spectrometry (GC – MS), proton (1H NMR), and carbon-13 ( 13C NMR) nuclear magnetic resonance methods.^

Subject Area

Chemistry, Organic

Recommended Citation

Maya Chen Wai, "Microwave-irradiated benzoylation reactions and coupling reactions" (2009). ETD Collection for Tennessee State University. Paper AAI1473393.
http://digitalscholarship.tnstate.edu/dissertations/AAI1473393

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