Regioselectively N-methylated azacalix[8]arene octamethyl ether prepared by catalytic aryl amination reaction using a temporal N-silylation protocol.
[Structure: see text] A temporal N-silylation protocol in the catalytic aryl amination reaction has been devised to prepare nitrogen-bridged calixarene analogues. The protocol involves a smooth in situ N-silylation before aryl amination reaction, followed by spontaneous cleavage of the N-Si bond in the usual workup process, to furnish secondary aromatic amines as the cross-coupled product with no silyl group on the nitrogen atom. A successful application to the preparation of regioselectively N-methylated azacalix[8]arene is described, together with the crystallographic analysis.
Ishibashi
Koichi
K
Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Tsue
Hirohito
H
Tokita
Satoshi
S
Matsui
Kazuhiro
K
Takahashi
Hiroki
H
Tamura
Rui
R
D000586:Amination; D002384:Catalysis; D008745:Methylation; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*
D019158:N-Acetylneuraminic Acid