Acid, Silver, and Solvent-Free Gold-Catalyzed Hydrophenoxylation of Internal Alkynes

Authors

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

Publication Date

2013

Description

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.

Journal

Beilstein Journal of Organic Chemistry

Volume

9

First Page

2002

Last Page

2008

Department

Chemistry

Link to Published Version

dx.doi.org/10.3762/bjoc.9.235

Recommended Citation

Richard, Marcia E.; Fraccica, Daniel V.; Garcia, Kevin J.; Miller, Erica J.; Ciccarelli, Rosa M.; Holahan, Erin C.; Resh, Victoria L.; Aakash, Shah; Findesi, Peter M.; and Stockland, Robert A. Jr.. "Acid, Silver, and Solvent-Free Gold-Catalyzed Hydrophenoxylation of Internal Alkynes." Beilstein Journal of Organic Chemistry (2013) : 2002-2008.