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Open Access Publications from the University of California

Intramolecular C(sp3 )-H Bond Oxygenation by Transition-Metal Acylnitrenoids.

  • Author(s): Tan, Yuqi
  • Chen, Shuming
  • Zhou, Zijun
  • Hong, Yubiao
  • Ivlev, Sergei
  • Houk, KN
  • Meggers, Eric
  • et al.

This study demonstrates for the first time that easily accessible transition-metal acylnitrenoids can be used for controlled direct C(sp3 )-H oxygenations. Specifically, a ruthenium catalyst activates N-benzoyloxycarbamates as nitrene precursors towards regioselective intramolecular C-H oxygenations to provide cyclic carbonates, hydroxylated carbamates, or 1,2-diols. The method can be applied to the chemoselective C-H oxygenation of benzylic, allylic, and propargylic C(sp3 )-H bonds. The reaction can be performed in an enantioselective fashion and switched in a catalyst-controlled fashion between C-H oxygenation and C-H amination. This work provides a new reaction mode for the regiocontrolled and stereocontrolled conversion of C(sp3 )-H into C(sp3 )-O bonds.

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