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Palladium‐Catalyzed Domino Process to Construct 2,3,9,9 a ‐Tetrahydro‐1 H ‐Fluorene Derivatives:Transient σ‐Alkylpalladium(II) Complex Mediated C(sp 2 )‐H Bond Activation
Author(s) -
Chi Xiaochen,
Meng Long,
Pang Qingyang,
Guo Lianfeng,
Liu Qing,
Zhao Pingping,
Zhang Daopeng,
Sun Fenggang,
Li Xinjin,
Liu Hui
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900600
Subject(s) - chemistry , palladium , intramolecular force , chemoselectivity , fluorene , cascade reaction , domino , medicinal chemistry , stereochemistry , metallacycle , catalysis , organic chemistry , polymer , x ray crystallography , physics , diffraction , optics
A palladium‐catalyzed cascade reaction involving domino Heck/intramolecular C−H arylation to construct 2,3,9,9 a ‐tetrahydro‐1 H ‐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(sp 2 )‐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.