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使用氰基硼氢化钠作为自由基介导物的流动 Giese 反应。

Flow Giese reaction using cyanoborohydride as a radical mediator.

机构信息

Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.

出版信息

Beilstein J Org Chem. 2013 Sep 3;9:1791-6. doi: 10.3762/bjoc.9.208. eCollection 2013.

Abstract

Tin-free Giese reactions, employing primary, secondary, and tertiary alkyl iodides as radical precursors, ethyl acrylate as a radical trap, and sodium cyanoborohydride as a radical mediator, were examined in a continuous flow system. With the use of an automated flow microreactor, flow reaction conditions for the Giese reaction were quickly optimized, and it was found that a reaction temperature of 70 °C in combination with a residence time of 10-15 minutes gave good yields of the desired addition products.

摘要

无锡的 Giese 反应,采用伯、仲、叔烷基碘化物作为自由基前体,丙烯酸乙酯作为自由基捕获剂,氰基硼氢化钠作为自由基介导剂,在连续流系统中进行了研究。使用自动化流动微反应器,快速优化了 Giese 反应的流动反应条件,发现反应温度为 70°C,停留时间为 10-15 分钟,可得到所需加成产物的良好收率。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/828a/3778382/2c8f5b80f324/Beilstein_J_Org_Chem-09-1791-g004.jpg

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