Document Type
Article
Version
Author's Final Manuscript
Publication Title
Organic Letters
Volume
18
Publication Date
12-2016
Abstract
A non-traditional approach to synthesizing aryl vinyl sulfides is described. 2,2-diphenyl-1,3-oxathiolane slowly liberates vinyl sulfide anion under basic conditions. Using a Pd/Xantphos catalyst system to activate a wide range of aryl bromides, this transient sulfide species can be effectively trapped and fed into a traditional Pd0/PdII catalytic cycle. Scope and limitations of the methodology are presented along with significant discussion of a competitive C–S bond activation by this catalyst system.
Publisher's Statement
© ACS 2016. This is the author's version of the work. It is posted here by permission of ACM for your personal use. Not for redistribution. The final published version can be found here: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b03249
Citation
Schmink, J.R. et al. 2016. Palladium-Catalyzed Synthesis of Aryl Vinyl Sulfides via 1,3-Oxathiolanes As Vinyl Sulfide Surrogates. Organic Letters 18.24:6360-6363.
DOI
http://www.doi.org/10.1021/acs.orglett.6b03249