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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
Synthesis of Acenes by Mechanochemical Reductive Aromatization
Zachary W Schroeder1, Madeline Lietz1, Michael J Ferguson2
1Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2, Canada.
Abstract:
A Sn-mediated mechanochemical reductive aromatization of 1,4-dihydroxy- and 1,4-dimethoxy-cyclohexadienes has been used to form 12 acenes, including derivatives of benzene, anthracene, tetracene, pentacene, and anthradithiophene. This method has been developed to overcome issues faced during the formation of electron-deficient 1,4-dihydroxy- or 1,4-dimethoxy-cyclohexadienes under homogeneous conditions. While this method does not tolerate trimethylsilyl protecting groups for alkynes, it can provide a fast and easily set up alternative to homogeneous reductive aromatization.
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