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二芳基碘鎓盐促进的烯烃芳基化反应

Three-Component Reactions of Diazoesters, Aldehydes, and Imines Using a Dual Catalytic System Consisting of a Rhodium(II) Complex and a Lewis Acid.

机构信息

Department of Materials Chemistry, Faculty of Engineering , Shinshu University , 4-17-1 Wakasato , Nagano 380-8553 , Japan.

出版信息

Org Lett. 2018 May 4;20(9):2659-2662. doi: 10.1021/acs.orglett.8b00865. Epub 2018 Apr 19.

DOI:10.1021/acs.orglett.8b00865
PMID:29671597
Abstract

A dual catalytic system, dirhodium tetrapivalate/ytterbium(III) triflate, enables the three-component reactions of α-alkyl-α-diazoesters, aromatic aldehydes, and N-benzylidenebenzylamine derivatives to afford the corresponding β-amino alcohols in good yields after hydrolysis of the oxazolidine cycloadducts, whereas no β-amino alcohols are obtained in the absence of ytterbium(III) triflate. A similar dual catalytic system, dirhodium tetraacetate/ytterbium(III) triflate, is found to be effective in accelerating the reactions of α-aryl-α-diazoesters in high yields. Furthermore, the reactions using dimethyl diazomalonate are described.

摘要

双催化体系,二钌四戊酸酯/三氟甲磺酸镱,使得α-烷基-α-重氮酯、芳香醛和 N-亚苄基苯甲胺衍生物的三组分反应能够在水解恶唑烷环加成物后以良好的收率得到相应的β-氨基醇,而在没有三氟甲磺酸镱的情况下则得不到β-氨基醇。类似的双催化体系,二醋酸钌/三氟甲磺酸镱,被发现有效地加速α-芳基-α-重氮酯的反应,收率很高。此外,还描述了使用二甲基重氮丙二酸酯的反应。

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