- Main
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.
Published Web Location
https://doi.org/10.1002/anie.202009335Abstract
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.
Many UC-authored scholarly publications are freely available on this site because of the UC's open access policies. Let us know how this access is important for you.