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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Visible-Light-Induced Sulfur-Alkenylation of Alkenes
Qi Xu1, Xiaoxuan Zhou1, Si Zhang1
1Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Abstract:
A visible-light-induced intermolecular sulfur-alkenylation of alkenes, including both activated and unactivated alkenes, is described. This sulfur-alkenylation reaction proceed in a highly regio- and stereospecific manner involving the visible-light-induced conversion of a ketene dithioacetal to the thiavinyl 1,3-dipole intermediate, followed by a formal [3 + 2] cycloaddition and C-S bond cleavage. Furthermore, it is also an efficient approach for the late-stage functionalization of natural products and complex molecules, even being induced by sunlight under ambient conditions.
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