Presentation Title

Kinetic and mechanistic investigations of gold-catalyzed Friedel–Crafts-like reactions of benzylic alcohols

Faculty Mentor

Robert Iafe

Start Date

23-11-2019 10:45 AM

End Date

23-11-2019 11:00 AM

Location

Markstein 205

Session

oral 2

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

Homogenous gold catalysis is increasingly being used as a cost-efficient and cost-effective strategy in the production of pharmaceutical products and their precursors. While the use of gold as a catalyst has previously been known to activate π bonds, upon microwave irradiation we have found gold to act as a Bronsted acid in the presence of silver as a co-catalyst. This discovery lead to the successful promotion of a microwave-assisted gold-catalyzed Friedel–Crafts-like reaction of benzylic alcohols with various nucleophiles, such as p-methylanisole and 1,2,3-benzotriazole. Efforts focused on the synthesis of these dynamic building blocks can be attributed to their widespread applications in pharmaceuticals, material science, and natural product synthesis. The prevalence of the 1,1-diarylalkane and triazole structural motifs in many anti-cancer, anti-inflammatory, antifungal, and antiviral drugs has driven the application of our novel synthesis method to afford these bioactive constituents with equal or better activity than the current pharmaceutical remedies. Considering the high regioselectivity and excellent yields (34-99%) achieved with optimal reaction conditions, we seek to discover more about the behavior of the gold(I) catalyst and its role in product formation through kinetic and mechanistic studies.

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Nov 23rd, 10:45 AM Nov 23rd, 11:00 AM

Kinetic and mechanistic investigations of gold-catalyzed Friedel–Crafts-like reactions of benzylic alcohols

Markstein 205

Homogenous gold catalysis is increasingly being used as a cost-efficient and cost-effective strategy in the production of pharmaceutical products and their precursors. While the use of gold as a catalyst has previously been known to activate π bonds, upon microwave irradiation we have found gold to act as a Bronsted acid in the presence of silver as a co-catalyst. This discovery lead to the successful promotion of a microwave-assisted gold-catalyzed Friedel–Crafts-like reaction of benzylic alcohols with various nucleophiles, such as p-methylanisole and 1,2,3-benzotriazole. Efforts focused on the synthesis of these dynamic building blocks can be attributed to their widespread applications in pharmaceuticals, material science, and natural product synthesis. The prevalence of the 1,1-diarylalkane and triazole structural motifs in many anti-cancer, anti-inflammatory, antifungal, and antiviral drugs has driven the application of our novel synthesis method to afford these bioactive constituents with equal or better activity than the current pharmaceutical remedies. Considering the high regioselectivity and excellent yields (34-99%) achieved with optimal reaction conditions, we seek to discover more about the behavior of the gold(I) catalyst and its role in product formation through kinetic and mechanistic studies.