Halogen Bond‐Catalyzed Friedel−Crafts Reactions of Furans Using a 2,2’‐Bipyridine‐Based Catalyst,Advanced Synthesis & Catalysis

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Halogen Bond‐Catalyzed Friedel−Crafts Reactions of Furans Using a 2,2’‐Bipyridine‐Based Catalyst
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-11-04 , DOI: 10.1002/adsc.202001019
Huimiao Zhang ₁ , Patrick H. Toy ₁

Affiliation

A halogen bond donor based on a 2,2’‐bipyridine framework has been synthesized, and used to catalyze Friedel−Crafts reactions of furans. Electrophiles used successfully in these reactions included various enones, an aldehyde, and a carboxylic acid anhydride. The yields of the reactions were generally good using a moderate catalyst loading (0.025 or 0.1 equiv.) at a relatively low temperature (room temp. or 50 °C) in acetonitrile. The catalyst used was designed with a biaryl scaffold so that if it indeed proved to be an efficient halogen bond donor organocatalyst, an enantioenriched version of it could potentially serve as a stereoselective catalyst.

中文翻译：

使用2,2'-联吡啶为基础的催化剂进行呋喃的卤素键催化的Friedel-Crafts反应

基于2，2'-联吡啶骨架的卤素键供体已经合成，并用于催化呋喃的Friedel-Crafts反应。在这些反应中成功使用的亲电试剂包括各种烯酮，醛和羧酸酐。在相对较低的温度（室温或50℃）下，在乙腈中使用适度的催化剂负载量（0.025或0.1当量），反应的收率通常很高。使用的催化剂设计有联芳基支架，因此，如果确实证明它是有效的卤素键供体有机催化剂，则其对映体富集的形式可能会用作立体选择性催化剂。

更新日期：2021-01-05

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