Homogeneous catalytic aminocarbonylation of 1-iodo-1-dodecene.: The facile synthesis of odd-number carboxamides via palladium-catalysed aminocarbonylation

被引：14

作者：

Takacs, Attila ^{[1
]}

Acs, Peter ^{[1
]}

Farkas, Roland ^{[1
]}

Kokotos, George ^{[2
]}

Kollar, Laszlo ^{[1
]}

机构：

[1] Univ Pecs, Dept Inorgan Chem, H-7624 Pecs, Hungary

[2] Univ Athens, Organ Chem Lab, GR-15771 Athens, Greece

来源：

TETRAHEDRON | 2008年 / 64卷 / 42期

关键词：

aminocarbonylation; carbon monoxide; iodoalkene; amino acid; palladium;

D O I：

10.1016/j.tet.2008.08.022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various amine nucleophiles including glycine methyl ester were used in the palladium-catalysed aminocarbonylation of (E)- and (Z)-1-iodo-1-dodecene. The substrates were synthesised from 1-dodecanal via the corresponding hydrazone, which was treated with iodine in the presence of tetramethylguanidine. The homogeneous catalytic aminocarbonylation resulted in the corresponding odd-number carboxamides in moderate to good yields. The reaction was accompanied by the formation of some carboxamides with triple bonds in the 2-position. The latter products were formed in relatively high yields with secondary amines such as piperidine and morpholine and were isolated as pure compounds. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：9874 / 9878

页数：5

共 34 条

[1] EVIDENCE FOR THE LIGATION OF PALLADIUM(0) COMPLEXES BY ACETATE IONS - CONSEQUENCES ON THE MECHANISM OF THEIR OXIDATIVE ADDITION WITH PHENYL IODIDE AND PHPD(OAC)(PPH(3))(2) AS INTERMEDIATE IN THE HECK REACTION [J].