4.7 Article

Palladium-catalyzed cascade metallo-ene/Suzuki coupling reaction of allenamides

Journal

CHEMICAL COMMUNICATIONS
Volume 53, Issue 21, Pages 3138-3141

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc00191f

Keywords

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Funding

  1. National Natural Science Foundation of China [21302057, 21405095]
  2. Young Talents Joint Fund of Shandong Province [ZR2015JL005]
  3. CPSF [2016M590736]
  4. Postdoctoral Innovation Project of Shandong Province [201501002]
  5. Technology Project of General Administration of Quality Supervision, Inspection and Quarantine [2016IK202]
  6. Zibo Positive Additive Co., Ltd

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A new type of cascade metallo-ene/Suzuki coupling reaction of allenamides catalyzed by palladium is described. A variety of polyfunctionalized 2,3-dihydropyrrole derivatives, which are important structural motifs for bioactive molecules, were furnished with excellent yields. Two new Csp(3)-Csp(2) bonds were constructed in one pot efficiently. The reductive elimination from p-allyl palladium complex presented excellent regioselectivity to the terminal C1 position. The unique terminal alkene was one of the most easily functionalized groups, providing these molecules with a potential transformation to much more complicated molecules.

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