Expeditious synthesis of 1,1-diarylethylenes related to isocombretastatin A-4 (isoCA-4) via palladium-catalyzed arylation of N-tosylhydrazones with aryl triflates

被引：88

作者：

Treguier, Bret ^{[1
]}

Hamze, Abdallah ^{[1
]}

Provot, Olivier ^{[1
]}

Brion, Jean-Daniel ^{[1
]}

Alami, Mouad ^{[1
]}

机构：

[1] Univ Paris 11, BioCIS, CNRS, UMR 8076,Lab Chim Therapeut,Fac Pharm, F-92296 Chatenay Malabry, France

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 47期

关键词：

Aryl triflates; Tosylhydrazones; Palladium; Xphos ligand; 1,1-Diarylethylenes; Isocombretastatin A-4; CROSS-COUPLING REACTIONS; ANTINEOPLASTIC AGENTS; BIOLOGICAL EVALUATION; COMBRETASTATIN A-4; ANTITUMOR-ACTIVITY; ANALOGS; DERIVATIVES; POTENT; TRANSFORMATIONS; INHIBITORS;

D O I：

10.1016/j.tetlet.2009.09.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A quick and efficient entry to 1,1-charylethylenes via the reaction of polyoxygenated aryl N-tosylhydrazones with aryl triflates is described. The reaction employs the catalytic system Pd(OAc)(2)/XPhos, tBuOL(1) as the base and dioxane as the solvent. A variety of substituents on both the coupling partner's hydrazones and triflates are tolerated. This procedure provides a complementary route to existing methods for the access of 1,1-diarylethylenes of biological interest. (C) 2009 Elsevier Ltd All rights reserved

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页码：6549 / 6552

页数：4

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