Palladium-Catalyzed Domino Process to Construct 2,3,9,9a-Tetrahydro-1H-Fluorene Derivatives:Transient sigma-Alkylpalladium(II) Complex Mediated C(sp(2))-H Bond Activation

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 sigma-alkylpalladium(II) complex is the key intermediate, which media...

Full description

Saved in:
Bibliographic Details
Published inAsian journal of organic chemistry Vol. 8; no. 12; pp. 2201 - 2204
Main Authors Chi, Xiaochen, Meng, Long, Pang, Qingyang, Guo, Lianfeng, Liu, Qing, Zhao, Pingping, Zhang, Daopeng, Sun, Fenggang, Li, Xinjin, Liu, Hui
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.12.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIRECT ARYLATION
NATURAL-PRODUCTS
ALKYLATION
H ACTIVATION
2
9a-tetrahydro-1H-fluorene derivatives
C-H activation
3
domino reactions
palladium
9
CYCLOISOMERIZATION
METAL
transient complexes
Online AccessGet more information

Cover

More Information
Summary: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 sigma-alkylpalladium(II) complex is the key intermediate, which mediates the C(sp(2))-H bond activation via a six-metallacycle. According to a transient sigma-alkylpalladium(II) complex, the control experiment demonstrates that beta-H elimination is faster than C-H activation. The methodology shows high chemoselectivity and good functional group tolerance.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900600