Presentation Title

Organocatalyzed hydroamination of dienes to produce dihydroquinolines

Faculty Mentor

Anna Wenzel

Start Date

23-11-2019 10:00 AM

End Date

23-11-2019 10:45 AM

Location

259

Session

poster 3

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Nitrogen-containing compounds, especially those which contain chiral amines, are of particular importance to a variety of industries, including agriculture and medicine. One method through which these compounds can be synthesized is hydroamination, a reaction characterized by the direct addition of an amine to an unsaturated carbon-carbon bond. This atom-economical process uses readily available starting materials, making it an inexpensive, relatively environmentally friendly process.

Due to the high energetic barrier of the reaction, hydroamination requires the use of a catalyst to progress from the reactants to the products. Previous research has shown that Brønsted acids can catalyze the hydroamination reactions of various substrates with high yields and enantioselectivities. Organocatalysis—the category of catalysis that Brønsted acids fall under—is preferable to the use of metal catalysts due to the decreased cost, low environmental impact, and lesser potential for toxicity. Thus, finding a simple and inexpensive method to improve hydroamination using organocatalysts is an important goal for synthetic organic chemistry.

The Wenzel research groups is currently preparing a variety of substrates for testing with Brønsted acid catalysts. This research, in particular, explores the efficacy of Brønsted acids as organocatalysts for the intramolecular hydroamination reactions of various phenyl dienes to form dihydroquinolines. Preliminary research has shown that ammonium trifluoroacetate (10 mol%) in tetrachloroethane at 100 °C can afford 90% conversion to the desired hydroamination product in 24 h. Progress in the preparation of substrates to investigate this lead result will be discussed.

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Nov 23rd, 10:00 AM Nov 23rd, 10:45 AM

Organocatalyzed hydroamination of dienes to produce dihydroquinolines

259

Nitrogen-containing compounds, especially those which contain chiral amines, are of particular importance to a variety of industries, including agriculture and medicine. One method through which these compounds can be synthesized is hydroamination, a reaction characterized by the direct addition of an amine to an unsaturated carbon-carbon bond. This atom-economical process uses readily available starting materials, making it an inexpensive, relatively environmentally friendly process.

Due to the high energetic barrier of the reaction, hydroamination requires the use of a catalyst to progress from the reactants to the products. Previous research has shown that Brønsted acids can catalyze the hydroamination reactions of various substrates with high yields and enantioselectivities. Organocatalysis—the category of catalysis that Brønsted acids fall under—is preferable to the use of metal catalysts due to the decreased cost, low environmental impact, and lesser potential for toxicity. Thus, finding a simple and inexpensive method to improve hydroamination using organocatalysts is an important goal for synthetic organic chemistry.

The Wenzel research groups is currently preparing a variety of substrates for testing with Brønsted acid catalysts. This research, in particular, explores the efficacy of Brønsted acids as organocatalysts for the intramolecular hydroamination reactions of various phenyl dienes to form dihydroquinolines. Preliminary research has shown that ammonium trifluoroacetate (10 mol%) in tetrachloroethane at 100 °C can afford 90% conversion to the desired hydroamination product in 24 h. Progress in the preparation of substrates to investigate this lead result will be discussed.