Department

Division of Math and Science

First Advisor

Dr. Rocky Barney

Description

Benzylic amines represent an important class of chemical compound and serve a critical role in medicine, industry, materials science, and agriculture. Given the prevalence of benzylic amines in such diverse applications, the importance of methodologies that allow for the direct and efficient synthesis of amines from readily available reagents, and under mild conditions is evident. The traditional methods of amine synthesis from an alcohol require multiple steps, often call for excess amine, and may present hurdles if sensitive functional groups are present. Few examples of the direct synthesis of amines from alcohols exist, and those that have been reported generally require harsh conditions or expensive catalysts. There are several examples of benzylic alcohols being converted directly to a variety of functional groups using an appropriate nucleophile and Lewis acid. Sulfur, oxygen, and phosphorus nucleophiles have all been used successfully. The proposed research seeks to develop a parallel reaction sequence using amines as nitrogen nucleophiles and zinc iodide as the Lewis acid, effectively allowing for a direct conversion of benzyl alcohol to the corresponding benzylic amine. A range of primary, secondary, and tertiary amines will be explored, and the scope and limitations of the reaction will be determined.

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Oral Presentation, Wyoming INBRE

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Direct Conversion of Benzyl Alcohol to Amines via Lewis Acid Activation

Benzylic amines represent an important class of chemical compound and serve a critical role in medicine, industry, materials science, and agriculture. Given the prevalence of benzylic amines in such diverse applications, the importance of methodologies that allow for the direct and efficient synthesis of amines from readily available reagents, and under mild conditions is evident. The traditional methods of amine synthesis from an alcohol require multiple steps, often call for excess amine, and may present hurdles if sensitive functional groups are present. Few examples of the direct synthesis of amines from alcohols exist, and those that have been reported generally require harsh conditions or expensive catalysts. There are several examples of benzylic alcohols being converted directly to a variety of functional groups using an appropriate nucleophile and Lewis acid. Sulfur, oxygen, and phosphorus nucleophiles have all been used successfully. The proposed research seeks to develop a parallel reaction sequence using amines as nitrogen nucleophiles and zinc iodide as the Lewis acid, effectively allowing for a direct conversion of benzyl alcohol to the corresponding benzylic amine. A range of primary, secondary, and tertiary amines will be explored, and the scope and limitations of the reaction will be determined.