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- Title
Palladium‐Catalyzed Domino Process to Construct 2,3,9,9a‐Tetrahydro‐1H‐Fluorene Derivatives:Transient σ‐Alkylpalladium(II) Complex Mediated C(sp<sup>2</sup>)‐H Bond Activation.
- Authors
Chi, Xiaochen; Meng, Long; Pang, Qingyang; Guo, Lianfeng; Liu, Qing; Zhao, Pingping; Zhang, Daopeng; Sun, Fenggang; Li, Xinjin; Liu, Hui
- Abstract
A palladium‐catalyzed cascade reaction involving domino Heck/intramolecular C−H arylation to construct 2,3,9,9a‐tetrahydro‐1H‐fluorene derivatives was developed. Products are obtained in moderate to excellent yields. The transient σ‐alkylpalladium(II) complex is the key intermediate, which mediates the C(sp2)‐H bond activation via a six‐metallacycle. According to a transient σ‐alkylpalladium(II) complex, the control experiment demonstrates that β‐H elimination is faster than C−H activation. The methodology shows high chemoselectivity and good functional group tolerance.
- Subjects
HECK reaction; FUNCTIONAL groups; ARYLATION; CHEMOSELECTIVITY
- Publication
Asian Journal of Organic Chemistry, 2019, Vol 8, Issue 12, p2201
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201900600