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

共 50 条

[41] Polymer-supported Lewis bases for the Baylis-Hillman reaction
Huang, JW
Shi, M
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) : 953 - 958
[42] Polymer-supported β-bromoethyl selenide:: An efficient reagent for the synthesis of aryl vinyl ethers
Sheng, SR
Liu, XL
Wang, XC
Xin, Q
Song, CS
SYNTHESIS-STUTTGART, 2004, (17): : 2833 - 2836
[43] Mesostructured polymer-supported diphenylphosphine-palladium complex: An efficient and recyclable catalyst for Heck reactions
Yao, Chengfu
Li, Haigang
Wu, Haihong
Liu, Yueming
Wu, Peng
CATALYSIS COMMUNICATIONS, 2009, 10 (07) : 1099 - 1102
[44] POLYMER-SUPPORTED BASES .3. SYNTHESIS OF PHOSPHATIDYLCHOLINES USING POLYMER-SUPPORTED AMINOPYRIDINES
TOMOI, M
GOTO, M
KAKIUCHI, H
NOGUCHI, Y
MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1985, 6 (06): : 397 - 401
[45] Palladium(0)-catalyzed coupling-cyclization reaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. Solid-phase parallel synthesis of butenolides
Ma, SM
Duan, DH
Wang, YZ
JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (03): : 239 - 247
[46] Palladium-catalyzed δ-selective reductive Heck reaction of alkenyl carbonyl compounds with aryl iodides and bromides
Li, Yang
Gong, Jun-Fang
Song, Mao-Ping
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (16) : 2216 - 2223
[47] SYNTHESIS OF POLYMER-SUPPORTED AND SILICA-SUPPORTED MANGANESE PHOSPHINE COMPLEXES AND THEIR REACTION WITH OXYGEN
LI, GQ
GOVIND, R
INORGANICA CHIMICA ACTA, 1995, 230 (1-2) : 219 - 223
[48] Radioiodination of polymer-supported organotrifluoroborates
Yong, Li
Yao, Min-Liang
Kelly, Hall
Green, James F.
Kabalka, George W.
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2011, 54 (04): : 173 - 174
[49] POLYMER-SUPPORTED CHAIN HOMOLOGATION
REGEN, SL
KODOMARI, M
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) : 1428 - 1429
[50] A polymer-supported thionating reagent
Ley, SV
Leach, AG
Storer, RI
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (04): : 358 - 361

← 1 2 3 4 5 →