Palladium-Catalyzed Synthesis of Aryl Vinyl Sulfides via 1,3-Oxathiolanes As Vinyl Sulfide Surrogates
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- 作者：Jason R. SchminkSummer A. Baker Dockrey ; Tianyi Zhang ; Naomi Chebet ; Alexis van Venrooy ; Mary Sexton ; Sarah I. Lew ; Steffany Chou ; Ami Okazaki
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：December 16, 2016
- 年：2016
- 卷：18
- 期：24
- 页码：6360-6363
- 全文大小：404K
- ISSN：1523-7052
文摘
A nontraditional approach to synthesizing aryl vinyl sulfides is described. 2,2-Diphenyl-1,3-oxathiolane slowly liberates a 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.