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Palladium(0)-Catalyzed coupling-cyclizationreaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. Solid-phase parallel synthesis of butenolides
其他题名钯催化的聚合为装载的芳基卤化物与1,2-联烯基羧酸的偶联-关环反应.丁烯酸内酯的固相合成
Ma SM(麻生明); Duan DH(段德慧); Wang YZ(王意中)
2002
发表期刊J. Comb. Chem.
ISSN1520-4766
卷号4期号:3页码:239-247
摘要In this contribution, we constructed a library of butenolides with 77 members by parallel synthesis strategy on merrifield resin. Sixtenn 2,3-allenoic acids and 12 polymer-bound aryl iodides were combined to react with each other, and then the polymer-supported products were cleaved to release butenolide dervatives. The reactions with alkyl-substituted 2,3-allenoic acids in acetonitrile afforded the corresponding products in high yields and high purities, whereas those with ary-substituted acids in acetonitrile failed. After some reaction conditions were screened, the solid-phase reactions with aryl-substituted 2,3-allenoic acids were realized in toluene, and the products areof good purities albeit in slightly low yields. In the benzyl ether linkage, a new cleavage model was found, By adding 6 equiv of acetyl bromide, we can get single(5-oxo-2,5-dihydrofuran-3-yl)benzyl bromide other than the corresponding benzyl acetate. To further increase the diversities, a dihydropyran (DHP) linker was introduced into our combinatorial synthesis of butenolides. By reversing the addition sequence of 2,3-allenoic acids and organic base, we realized the solid-phase cyclization reaction of polymer-bound aryliodides with the THP linkage in moderate yields and good purities now the library of butenolides includes (5-oxo-2,5-dihydrofuran-3-yl)benzoic acids, -aryl acetates, -benzyl bromides, -benzyl alcohols, and -phenols, which are difficult to synthesize with conventional solution methods.
学科领域金属有机化学
部门归属中国科学院上海有机化学研究所金属有机化学开放实验室
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收录类别SCI
语种英语
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/11880
专题金属有机化学国家重点实验室
通讯作者Ma SM(麻生明)
推荐引用方式
GB/T 7714
Ma SM,Duan DH,Wang YZ. Palladium(0)-Catalyzed coupling-cyclizationreaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. Solid-phase parallel synthesis of butenolides[J]. J. Comb. Chem.,2002,4(3):239-247.
APA 麻生明,段德慧,&王意中.(2002).Palladium(0)-Catalyzed coupling-cyclizationreaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. Solid-phase parallel synthesis of butenolides.J. Comb. Chem.,4(3),239-247.
MLA 麻生明,et al."Palladium(0)-Catalyzed coupling-cyclizationreaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. Solid-phase parallel synthesis of butenolides".J. Comb. Chem. 4.3(2002):239-247.
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