Presentation Title

Microwave-Assisted Gold-Catalyzed Reaction of Benzylic Alcohols: Mechanistic and Kinetic Investigations

Faculty Mentor

Dr. Robert G Iafe

Start Date

23-11-2019 8:45 AM

End Date

23-11-2019 9:00 AM

Location

Markstein 205

Session

oral 1

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

Gold-catalyzed reactions are becoming more ubiquitous as key bond-forming steps due to their unique reactivity. Of these unique reactions, we have demonstrated that gold(I) salts, activated by halide abstraction, catalyze the substitution reaction of benzylic alcohols with electron-rich aromatic compounds (nucleophile = phenol, 1,2,3-benzotriazole). We present a mechanistic study on the gold-catalyzed displacement reaction of benzylic alcohols through a combination of spectroscopic, synthetic, and kinetic approaches. We report that these reactions are first order in nature, and proceed via an sp2-hybridized intermediate. Control reactions with acid scavengers and alternate acid sources have been used to support catalysis by gold. Reactions with benzylic deuterium proceeded without isotopic erosion or scrambling. Most interesting is these gold-catalyzed reactions proceed with retention of stereochemistry. Complete mechanistic details will be presented.

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Nov 23rd, 8:45 AM Nov 23rd, 9:00 AM

Microwave-Assisted Gold-Catalyzed Reaction of Benzylic Alcohols: Mechanistic and Kinetic Investigations

Markstein 205

Gold-catalyzed reactions are becoming more ubiquitous as key bond-forming steps due to their unique reactivity. Of these unique reactions, we have demonstrated that gold(I) salts, activated by halide abstraction, catalyze the substitution reaction of benzylic alcohols with electron-rich aromatic compounds (nucleophile = phenol, 1,2,3-benzotriazole). We present a mechanistic study on the gold-catalyzed displacement reaction of benzylic alcohols through a combination of spectroscopic, synthetic, and kinetic approaches. We report that these reactions are first order in nature, and proceed via an sp2-hybridized intermediate. Control reactions with acid scavengers and alternate acid sources have been used to support catalysis by gold. Reactions with benzylic deuterium proceeded without isotopic erosion or scrambling. Most interesting is these gold-catalyzed reactions proceed with retention of stereochemistry. Complete mechanistic details will be presented.