4.6 Article

Metal-free decarbonylative alkylation-aminoxidation of styrene derivatives with aliphatic aldehydes and N-hydroxyphthalimide

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 6, Pages 1338-1342

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00030h

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Funding

  1. Opening Fund of Beijing National Laboratory for Molecular Sciences
  2. Xiangtan University [11QDZ20]
  3. Hunan Provincial Natural Science Foundation [2016JJ2122]
  4. Hunan Collaborative Innovation Centre of Chemical Engineering & Technology with Environmental Benignity and Effective Resource Utilization

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A convenient metal-free decarbonylative alkylation-aminoxidation of styrene derivatives with aliphatic aldehydes and N-hydroxyphthalimide (NHPI) to yield phthalimide protected alkoxyamines is developed. With DTBP as an oxidant and radical-initiator, this reaction smoothly converts aliphatic aldehydes into alkyl radicals and subsequently allows the cascade construction of C(sp(3))-C(sp(3)) and C(sp(3))-O bonds via radical-radical coupling.

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