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  • Title: Regioselectively N-methylated azacalix[8]arene octamethyl ether prepared by catalytic aryl amination reaction using a temporal N-silylation protocol.
    Author: Ishibashi K, Tsue H, Tokita S, Matsui K, Takahashi H, Tamura R.
    Journal: Org Lett; 2006 Dec 21; 8(26):5991-4. PubMed ID: 17165912.
    Abstract:
    [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.
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