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Chemistry

University of South Florida

2017

Alkynylation

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Hydroalkynylation Of Oxocarbenium Intermediates Via Au(I) Catalysis, Courtney Smith Smith Feb 2017

Hydroalkynylation Of Oxocarbenium Intermediates Via Au(I) Catalysis, Courtney Smith Smith

USF Tampa Graduate Theses and Dissertations

Au(I) catalysis has recently emerged as a powerful tool for the realization of a broad range of organic transformations. Despite this rapid development, attaining selectivity and maintaining catalyst stability remain significant challenges. Rational ligand design, such as the employment of NHC or TA ligands, has been used to confront these issues. This thesis focuses on the use of Au(I) catalysts bearing these ligands for the selective hydroalkynylation of enol ethers. By employing a TA-Au stabilized catalyst, [(OAr)3PAu(TA-H)]OTf, the intermolecular hydroalkynylation of enol ethers, a substrate that is well-known to promote decomposition of the gold cation, was efficiently achieved. …