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University of South Florida

2020

2-isoxazolines

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New Synthetic Methodology Using Base-Assisted Diazonium Salts Activation And Gold Redox Catalysis, Abiola Azeez Jimoh Apr 2020

New Synthetic Methodology Using Base-Assisted Diazonium Salts Activation And Gold Redox Catalysis, Abiola Azeez Jimoh

USF Tampa Graduate Theses and Dissertations

Over the past two decades, homogeneous Au(I) catalysis has been a valuable synthetic tool for activating a series of unsaturated carbon-carbon bonds towards nucleophilic attack. Despite this progress, Au(I/III) redox chemistry has not been well explored. This is largely due to the challenges associated with the high oxidation potential of gold. Hence, the need for an efficient and safe method for Au oxidation.

Herein, a base-assisted diazonium salt activation has been used to facilitate Au redox reactions under mild reaction conditions. This oxidative coupling method afforded functional isoxazolines with good to excellent yields, while the alternative photoactivation method provided trace …