The Heck reaction of polymer-supported allylamine with aryl iodides

被引：7

作者：

Leikoski, Tuomo ^{[1
]}

Wrigstedt, Pauli ^{[1
]}

Helminen, Jussi ^{[1
]}

Matikainen, Jorma ^{[1
]}

Sipila, Jussi ^{[1
]}

Yli-Kauhaluoma, Jari ^{[2
]}

机构：

[1] Univ Helsinki, Organ Chem Lab, Dept Chem, FI-00014 Helsinki, Finland

[2] Univ Helsinki, Div Pharmaceut Chem, Fac Pharm, FI-00014 Helsinki, Finland

来源：

TETRAHEDRON | 2013年 / 69卷 / 02期

基金：

芬兰科学院;

关键词：

Heck; Solid-phase; Polymer; Palladium; Allylamine; Cinnamylamine; SOLID-PHASE SYNTHESIS; PALLADIUM-CATALYZED SYNTHESIS; IODO BENZYL ENAMINES; STEREOSELECTIVE ARYLATION; MEDIATED CYCLIZATIONS; COUPLING STRATEGY; TRACELESS LINKER; C-C; EFFICIENT; PALLADACYCLES;

D O I：

10.1016/j.tet.2012.10.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Heck reaction of Wang resin-bound allylamine with aryl iodides produces various, substituted cinnamylamines. The catalyst and additive system consisting of palladium(II) acetate, n-Bu4NOAc and potassium chloride, in addition to potassium carbonate in N,N-dimethylformamide, accomplishes a regioselective gamma-arylation. By utilising the easily formed and stable carbamate linker on Wang resin, the incompatibility of free amines with the palladium catalyst is avoided. The cinnamylamine products are cleaved from the resin with trifluoroacetic acid under mild conditions and are converted into chromatographically separable acetamides. Our solid-phase method offers a new alternative for the synthesis of cinnamylamine derivatives, as biologically interesting compounds and useful synthetic intermediates. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：839 / 843

页数：5

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