One-pot synthetic routes to multiply substituted indene derivatives by hydrolysis of zirconocene-mediated intermolecular coupling reactions of aromatic ketones and alkynes.
Two one-pot multicomponent synthetic methods for highly substituted indenes are described. The intermolecular coupling of aromatic ketones with alkynes on low-valent zirconocene species generates oxazirconacyclopentenes, which upon hydrolysis with 20% HCl for 3 h afforded indene derivatives in good to excellent yields. Similarly, the pair-selective coupling of two identical or different alkynes bearing at least one aromatic substituent formed zirconacyclopentadienes. Quenching of the reaction mixture with concentrated H(2)SO(4) also results in the formation of highly substituted indenes in high yields.
Xi
Zhenfeng
Z
Peking University-Hokkaido University Joint Lab, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China.
Guo
Ruiyun
R
Mito
Shizue
S
Yan
Hongliang
H
Kanno
Ken-ichiro
K
Nakajima
Kiyohiko
K
Takahashi
Tamotsu
T