Event Title

Microwave-Assisted Hydrogenations Using Frustrated Lewis Pairs

Presenter Information

Yilan Miao

Faculty Advisor

Elizabeth Valentin

Start Date

24-4-2018 5:00 PM

End Date

24-4-2018 6:00 PM

Description

Frustrated Lewis pairs (FLP) consist of sterically hindered Lewis acid and base, for which the formation of classical Lewis acid-base adducts do not form. Within one decade, the metal-free catalytic hydrogenation has rapidly managed to progress, and the substrate scope has been broadened to a wide variety of functional groups, such as heterocycles, aldehydes, and ketones. However, the strict anhydrous reaction conditions and sensitivity for other functional groups for FLP-catalyzed hydrogenation has seriously limited the applications of this methodology, which prevented FLPs from being truly viable alternatives for transition metal hydrogenation catalysts. In this study, a more applicable and efficient Green Chemistry technique, microwave irradiation, was used as the source of heat. By transferring heat directly to a closed system, the reaction time was significantly reduced. Cyclopentyl methyl ether (CPME) was identified as the most efficient solvent among those tested. Other optimal reaction parameters, such as temperature, and pressure were also studied. High yields were achieved under the experimental conditions. The scope and limitations of this methodology will be presented.

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Apr 24th, 5:00 PM Apr 24th, 6:00 PM

Microwave-Assisted Hydrogenations Using Frustrated Lewis Pairs

Frustrated Lewis pairs (FLP) consist of sterically hindered Lewis acid and base, for which the formation of classical Lewis acid-base adducts do not form. Within one decade, the metal-free catalytic hydrogenation has rapidly managed to progress, and the substrate scope has been broadened to a wide variety of functional groups, such as heterocycles, aldehydes, and ketones. However, the strict anhydrous reaction conditions and sensitivity for other functional groups for FLP-catalyzed hydrogenation has seriously limited the applications of this methodology, which prevented FLPs from being truly viable alternatives for transition metal hydrogenation catalysts. In this study, a more applicable and efficient Green Chemistry technique, microwave irradiation, was used as the source of heat. By transferring heat directly to a closed system, the reaction time was significantly reduced. Cyclopentyl methyl ether (CPME) was identified as the most efficient solvent among those tested. Other optimal reaction parameters, such as temperature, and pressure were also studied. High yields were achieved under the experimental conditions. The scope and limitations of this methodology will be presented.