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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
Lithium Diisopropylamide Catalyzed Allylic C-H Bond Alkylation with Styrenes
Xiang-Yu Zhang1, Lei Zheng1, Bing-Tao Guan1,2
1State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry , Nankai University , Tianjin 300071 , China.
Abstract:
Allylic substitution reactions, a well-established approach for new bond construction, often need transition-metal catalysts and stoichiometric amounts of organometallic reagents, strong bases, or oxidants. Lithium diisopropylamide (LDA), a widely used and commercially available Brønsted base, is herein reported to catalyze the allylic C-H bond addition of 1,3-diarylpropenes to styrenes. Preliminary mechanism studies have provided a solid structure of the π-allyllithium intermediate and revealed the unique catalytic roles of LDA and its conjugate acid diisopropylamine.
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