Regioselectively N-Methylated Azacalix[8]arene Octamethyl Ether Prepared by Catalytic Aryl Amination Reaction Using a Temporal N-Silylation Protocol
Organic Letters2006Vol. 8(26), pp. 5991–5994
Citations Over TimeTop 10% of 2006 papers
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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