Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions

被引：13

作者：

da Costa, Rafaela G. M. ^{[1
]}

Farias, Francisco R. L. ^{[1
]}

Back, Davi ^{[2
]}

Limberger, Jones ^{[1
]}

机构：

[1] Pontificial Catolic Univ Rio De Janeiro, Dept Chem, Rua Marques Sao Vicente 225, BR-22451900 Rio De Janeiro, RJ, Brazil

[2] Univ Fed Santa Maria, Dept Chem, Lab Inorgan Mat, Av Roraima 1000, BR-97105900 Santa Maria, RS, Brazil

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 08期

关键词：

Chalcone; Cross-coupling; Heck reaction; Tetra-substituted olefin; Suzuki coupling; Palladium; CATALYZED HECK REACTIONS; TETRASUBSTITUTED OLEFINS; VINYLATION; ALKENES; HALIDES; ACIDS;

D O I：

10.1016/j.tetlet.2018.01.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A useful protocol for arylation of the olefin double bond of chalcones to afford tri- and tetra-substituted chalcone derivatives is reported. The protocol begins with the Heck reaction between chalcones and aryl iodides providing beta-arylchalcones. This reaction tolerates various functional groups on both rings, as well as deactivated aryl iodides. The products are obtained in moderate to excellent yields and the (E)-beta-arylchalcones (E:Z > 96:4) can be isolated via precipitation. Competitive Heck reactions pointed to a significant effect of ring one substituents on the reaction rate, while substituents on ring two have a much smaller effect. To access alpha,beta-diarylchalcones, a sequential bromination-Suzuki cross coupling strategy was applied to the beta-arylated compounds which afforded double arylated chalcone derivatives in 60-99% yield over two steps. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：771 / 775

页数：5

共 35 条

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