Catalytic construction and reconstruction of guanidines: Ti-mediated guanylation of amines and transamination of guanidines

被引：179

作者：

Ong, TG

Yap, GPA

Richeson, DS ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

[2] Univ Ottawa, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 27期

关键词：

D O I：

10.1021/ja035716j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bis(guanidinate) titanium imido complexes [{(Me2N)C(NiPr)2}2TiNAr-] (Ar- = 2,6-Me2C6H3 (1a); C6F5 (1b)) are competent catalysts for the guanylation of a variety of arylamines with carbodiimide. The reversible [2 + 2] addition of iPrN=C=NiPr to 1b is demonstrated and is proposed to be part of the catalytic cycle. Compounds 1a and 1b are also effective precatalysts for the transamination of trialkylguanidines with arylamines to yield aryldialkylguanidines. Copyright © 2003 American Chemical Society.

引用

收藏

页码：8100 / 8101

页数：2

相关论文

共 46 条

[1] A highly reactive titanium precatalyst for intramolecular hydroamination reactions [J].

Ackermann, L ;

Bergman, RG .

ORGANIC LETTERS, 2002, 4 (09) :1475-1478

[2] VARIABLE REGIOCHEMISTRY IN THE STOICHIOMETRIC AND CATALYTIC HYDROAMINATION OF ALKYNES BY IMIDOZIRCONIUM COMPLEXES CAUSED BY AN UNUSUAL DEPENDENCE OF THE RATE LAW ON ALKYNE STRUCTURE AND TEMPERATURE [J].

BARANGER, AM ;

WALSH, PJ ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2753-2763

[3] Synthesis and imido-group exchange reactions of tert-butylimidotitanium complexes [J].

Blake, AJ ;

Collier, PE ;

Dunn, SC ;

Li, WS ;

Mountford, P ;

Shishkin, OV .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (09) :1549-1558

[4]

Bytschkov I, 2003, EUR J ORG CHEM, V2003, P935

[5] A titanium-catalyzed three-component coupling to generate α,β-unsaturated β-iminoamines [J].

Cao, CS ;

Shi, YH ;

Odom, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2880-2881

[6] Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines [J].

Cao, CS ;

Shi, YH ;

Odom, AL .

ORGANIC LETTERS, 2002, 4 (17) :2853-2856

[7] PREPARATION AND PROPERTIES OF TANTALUM IMIDO COMPLEXES AND THEIR REACTIONS WITH ALKYNES - COORDINATION CONTROL THROUGH MULTIPLE METAL-LIGAND BONDING [J].

CHAO, YW ;

WEXLER, PA ;

WIGLEY, DE .

INORGANIC CHEMISTRY, 1989, 28 (20) :3860-3868

[8]

ELRED SE, 2003, J AM CHEM SOC, V125, P3422

[9] Scope of the intramolecular imidotitanium-alkyne [2+2] cycloaddition azatitanetine acylation sequence. An efficient procedure for the synthesis of 2-(2-keto-1-alkylidene)tetrahydropyrrole and related compounds [J].

Fairfax, D ;

Stein, M ;

Livinghouse, T ;

Jensen, M .

ORGANOMETALLICS, 1997, 16 (08) :1523-1525

[10] Diprotected triflylguanidines: A new class of guanidinylation reagents [J].

Feichtinger, K ;

Zapf, C ;

Sings, HL ;

Goodman, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3804-3805

← 1 2 3 4 5 →