Presentation Title

A microwave assisted gold-catalyzed substitution reaction of benzylic alcohols with benzimidazole

Faculty Mentor

Robert Iafe

Start Date

23-11-2019 10:30 AM

End Date

23-11-2019 10:45 AM

Location

Markstein 205

Session

oral 2

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

Benzimidazole and its derivatives are an important class of bioactive molecules that are found in small molecule drugs. With the rise of drug resistance, it is important to be able to quickly develop new compounds to help combat this resistance. Previously, our lab developed a methodology that uses gold salts and microwave irradiation to catalyze Friedel–Crafts-like reactions with benzylic alcohols. Currently, our lab is working to apply this methodology to use gold(I) salts to catalyze the displacement of benzylic alcohols with benzimidazole. We were able to synthesize several benzimidazole derivatives to use as nucleophiles in this reaction. These nucleophiles include N-tosyl-benzimidazole, N-benzyl-benzimidazole, and N-boc-benzimidazole. Each of these nucleophiles were synthesized at yields consistent or better than the corresponding literature. For the reaction, benzimidazole was able to displace the benzylic alcohol on the starting material, 1-phenylethanol, to synthesize the product, 1-(1-phenylethyl)-1H-benzimidazole, at 40% yield. All derivatives, except N-benzyl-benzimidazole, was able to synthesize the product. N-tosyl-benzimidazole synthesized the product at 7% yield and N-boc-benzimidazole synthesized the product at 75% yield. The synthesis of all products was confirmed using 1H and 13C NMR spectroscopy. The progress on the optimization of this reaction will be reported.

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Nov 23rd, 10:30 AM Nov 23rd, 10:45 AM

A microwave assisted gold-catalyzed substitution reaction of benzylic alcohols with benzimidazole

Markstein 205

Benzimidazole and its derivatives are an important class of bioactive molecules that are found in small molecule drugs. With the rise of drug resistance, it is important to be able to quickly develop new compounds to help combat this resistance. Previously, our lab developed a methodology that uses gold salts and microwave irradiation to catalyze Friedel–Crafts-like reactions with benzylic alcohols. Currently, our lab is working to apply this methodology to use gold(I) salts to catalyze the displacement of benzylic alcohols with benzimidazole. We were able to synthesize several benzimidazole derivatives to use as nucleophiles in this reaction. These nucleophiles include N-tosyl-benzimidazole, N-benzyl-benzimidazole, and N-boc-benzimidazole. Each of these nucleophiles were synthesized at yields consistent or better than the corresponding literature. For the reaction, benzimidazole was able to displace the benzylic alcohol on the starting material, 1-phenylethanol, to synthesize the product, 1-(1-phenylethyl)-1H-benzimidazole, at 40% yield. All derivatives, except N-benzyl-benzimidazole, was able to synthesize the product. N-tosyl-benzimidazole synthesized the product at 7% yield and N-boc-benzimidazole synthesized the product at 75% yield. The synthesis of all products was confirmed using 1H and 13C NMR spectroscopy. The progress on the optimization of this reaction will be reported.