Beilstein Journal of Organic Chemistry 2013-01-01

Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes.

Marcia E Richard, Daniel V Fraccica, Kevin J Garcia, Erica J Miller, Rosa M Ciccarelli, Erin C Holahan, Victoria L Resh, Aakash Shah, Peter M Findeis, Robert A Stockland Jr

Index: Beilstein J. Org. Chem. 9 , 2002-8, (2013)

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Abstract

A range of arylgold compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos or IPr/SIPr. Phenols bearing either electron-withdrawing or electron-donating groups were efficiently added using these catalysts. No silver salts, acids, or solvents were needed for the catalysis, and either microwave or conventional heating afforded moderate to excellent yields of the vinyl ethers.