HECK REACTION ON ANTHRAQUINONE DERIVATIVES - LIGAND, SOLVENT, AND SALT EFFECTS

被引：143

作者：

CABRI, W ^{[1
]}

CANDIANI, I ^{[1
]}

DEBERNARDINIS, S ^{[1
]}

FRANCALANCI, F ^{[1
]}

PENCO, S ^{[1
]}

SANTI, R ^{[1
]}

机构：

[1] IST GUIDO DONEGANI SPA,I-28100 NOVARA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 20期

关键词：

D O I：

10.1021/jo00020a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed Heck reaction of trifluoromethanesulfonates of anthraquinoid systems is described. The outcome of the reaction between methyl acrylate 4 and 1-(9,10-anthraquinoyl)trifluoromethanesulfonate 7 (reduction versus arylation) is strongly correlated to the choice of ligand, solvent, and added salt. The results are explained in terms of different coordination-insertion pathways as a function of the reaction conditions. Best conditions have been transferred to the synthesis of novel anthracyclinone, 4-demethoxy-4-(2'-methoxycarbonyl)ethenyl-13-dioxolanyldaunomycinone 5.

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页码：5796 / 5800

页数：5

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