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Palladium-Catalyzed Synthesis of Aryl Vinyl Sulfides via 1,3-Oxathiolanes As Vinyl Sulfide Surrogates

Jason R. Schmink* , Summer A. Baker Dockrey, Tianyi Zhang, Naomi Chebet, Alexis van Venrooy, Mary Sexton, Sarah I. Lew, Steffany Chou and Ami Okazaki

*Department of Chemistry, Bryn Mawr College, 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States, Email: jschminkbrynmawr.edu

J. R. Schmink, S. A. B. Dockrey, T. Zhang, N. Chebet, A. van Venrooy, M. Sexton, S. I. Lew, S. Chou, A. Okazaki, Org. Lett., 2016, 18, 6360-6363.

DOI: 10.1021/acs.orglett.6b03249 (free Supporting Information)


Abstract

2,2-Diphenyl-1,3-oxathiolane slowly liberates a vinyl sulfide anion under basic conditions, that can be effectively used in Pd/Xantphos-catalyzed reactions with a wide range of aryl bromides to provide aryl vinyl sulfides.

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Key Words

aryl sulfides, vinyl sulfides


ID: J54-Y2016