Presentation Title

Microwave-Assisted Gold-Catalyzed Reactions of Benzylic Alcohols with Heteroaromatic Nucleophiles

Faculty Mentor

Robert Iafe

Start Date

23-11-2019 9:30 AM

End Date

23-11-2019 9:45 AM

Location

Markstein 205

Session

oral 1

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

Benzimidazole and benzimidazole derivatives make up an important class of bioactive molecules called azoles and are present in small molecule drugs. Structurally, benzimidazoles contain a 5-membered aromatic ring with at least one nitrogen atom and are an important building block for therapeutic compounds. Catalytic methods for rapid preparation of these compounds are urgently needed to help address today’s most challenging biomedical problems, including resistance to drugs for cancer and infectious diseases. During a prior investigation using gold salts to catalyze etherification reactions, our lab discovered that electron-rich nitrogen-containing aromatic groups react via a Friedel–Crafts-like reaction mechanism instead of the etherification pathway. In this work we report that a microwave assisted methodology using gold(I) salts catalyze the displacement of benzylic alcohols with benzimidazole.

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Nov 23rd, 9:30 AM Nov 23rd, 9:45 AM

Microwave-Assisted Gold-Catalyzed Reactions of Benzylic Alcohols with Heteroaromatic Nucleophiles

Markstein 205

Benzimidazole and benzimidazole derivatives make up an important class of bioactive molecules called azoles and are present in small molecule drugs. Structurally, benzimidazoles contain a 5-membered aromatic ring with at least one nitrogen atom and are an important building block for therapeutic compounds. Catalytic methods for rapid preparation of these compounds are urgently needed to help address today’s most challenging biomedical problems, including resistance to drugs for cancer and infectious diseases. During a prior investigation using gold salts to catalyze etherification reactions, our lab discovered that electron-rich nitrogen-containing aromatic groups react via a Friedel–Crafts-like reaction mechanism instead of the etherification pathway. In this work we report that a microwave assisted methodology using gold(I) salts catalyze the displacement of benzylic alcohols with benzimidazole.