Highly Selective Monomethylation of Primary Amines Through Host-Guest Product Sequestration

被引：60

作者：

Yebeutchou, Roger M.

Dalcanale, Enrico ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 07期

关键词：

CATALYZED N-ALKYLATION; ACCELERATION; AMINOARENES; METHYLATION; CAVITANDS; ANILINES;

D O I：

10.1021/ja809614y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This Communication reports the highly selective monomethylation of primary amines through host-guest product sequestration. Complete control of the outcome of the N-methylation reaction has been achieved by adding to the reaction medium stoichiometric amounts of a teraphosphonate phosphonate cavitand Tiiii, capable of selectively and quantitatively trapping the monomethylated ammonium salt formed. The synergistic combination of ion-dipole, H-bonding, and CH3-pi interactions provide the high association constants (K-ass > 10(9)) and the specific complexation mode necessary for the exclusive sequestration of the monomethylated intermediate reaction product.

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页码：2452 / +

页数：3

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