HECK REACTION ON ANTHRAQUINONE DERIVATIVES - LIGAND, SOLVENT, AND SALT EFFECTS
HECK REACTION ON ANTHRAQUINONE DERIVATIVES - LIGAND, SOLVENT, AND SALT EFFECTS
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DOI：
10.1021/jo00020a020
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发表时间：
1991-09-27
影响因子：
3.6
通讯作者：
SANTI, R
中科院分区：
文献类型：
--
作者：
CABRI, W;CANDIANI, I;SANTI, R
介绍了钯催化的类蒽醌体系中三氟甲烷磺酸盐的Heck反应。丙烯酸甲酯4与1-（9,10-蒽醌基）三氟甲烷磺酸7的反应结果（还原与芳基化）与配体、溶剂和添加盐的选择密切相关。结果解释了不同的配位插入途径作为反应条件的函数。研究了合成新型蒽环类药物4-去甲氧基-4-（2′-甲氧基羰基）乙基-13-二氧基甲霉素酮5的最佳工艺条件。
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.