Presentation Title

The Microwave Assisted, Gold-Catalyzed Ritter-type Reaction

Faculty Mentor

Robert Iafe

Start Date

17-11-2018 10:30 AM

End Date

17-11-2018 10:45 AM

Location

C323

Session

Oral 2

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

Advances in amide synthesis has been vital to medicinal advancement, as the amide functional group is found in many of today’s life changing medications and used for treatment of HIV, cancer, hepatitis B, and much more. Our lab has recently developed methodology to couple benzylic alcohols with nucleophiles using gold(I) salts. Herein, we report the synthesis of secondary N-benzylamides by a microwave-assisted gold-catalyzed Ritter-type reaction of benzylic alcohols. Optimal reaction conditions were determined to be 5 mol % Ph3PAuCl as the gold(I) catalyst and 5 mol % AgSbF6 as the silver co-catalyst with microwave irradiation. Furthermore, our reaction methodology supports the growing literature of gold(I) having similar catalytic activity as the hydronium, a hard acid. Full details of catalyst loading investigations will be discussed, and extensive substrate scope explorations will be presented.

Summary of research results to be presented

Optimal reaction conditions were determined to be 5 mol % Ph3AuCl as the gold(I) catalyst and 5 mol % AgSbF6 in propionitrile. Electronic and steric factors were explored in this reaction, and can be summarized in the following: (1) electron-rich electrophiles performed well, whereas electron-deficient electrophiles had trouble; (2) linear benzylic alcohols resulted in very high yields of the resulting amide; and (3) sterically demanding benzylic alcohols hindered the reaction. 20 Different small molecule amide syntheses will be presented.

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Nov 17th, 10:30 AM Nov 17th, 10:45 AM

The Microwave Assisted, Gold-Catalyzed Ritter-type Reaction

C323

Advances in amide synthesis has been vital to medicinal advancement, as the amide functional group is found in many of today’s life changing medications and used for treatment of HIV, cancer, hepatitis B, and much more. Our lab has recently developed methodology to couple benzylic alcohols with nucleophiles using gold(I) salts. Herein, we report the synthesis of secondary N-benzylamides by a microwave-assisted gold-catalyzed Ritter-type reaction of benzylic alcohols. Optimal reaction conditions were determined to be 5 mol % Ph3PAuCl as the gold(I) catalyst and 5 mol % AgSbF6 as the silver co-catalyst with microwave irradiation. Furthermore, our reaction methodology supports the growing literature of gold(I) having similar catalytic activity as the hydronium, a hard acid. Full details of catalyst loading investigations will be discussed, and extensive substrate scope explorations will be presented.