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四氢呋喃:在石墨相氮化碳光催化的连续流动自由基环化反应中一种高效的电子供体。

THF: an efficient electron donor in continuous flow radical cyclization photocatalyzed by graphitic carbon nitride.

作者信息

Woźnica Magdalena, Chaoui Nicolas, Taabache Soraya, Blechert Siegfried

机构信息

Institute of Chemistry, Technical University Berlin, Strasse des 17. Juni 135, 10623 Berlin (Germany), Fax: +49 30 314 29745.

出版信息

Chemistry. 2014 Nov 3;20(45):14624-8. doi: 10.1002/chem.201404440. Epub 2014 Sep 24.

DOI:10.1002/chem.201404440
PMID:25252017
Abstract

Mesoporous graphitic carbon nitride (mpg-C3 N4 ) was found to be an efficient heterogeneous photocatalyst for the metal-free radical cyclization of 2-bromo-1,3-dicarbonyl compounds. Reactions leading to functionalized cyclopentanes proceed under mild conditions and can be conducted in a continuous flow photoreactor. Compared to the batch reaction, the use of a continuous flow reactor resulted in a significant reduction in reaction time (complete conversion of 0.04 mmol of substrate in a batch was achieved after 4 h, whereas in a flow reactor the same amount of substrate was fully converted into a product within 40 min). Mechanistic studies of the reaction showed that THF plays not only the role of solvent, but is also a crucial hydrogen and electron donor.

摘要

介孔石墨相氮化碳(mpg-C3N4)被发现是一种用于2-溴-1,3-二羰基化合物无金属自由基环化反应的高效多相光催化剂。生成官能化环戊烷的反应在温和条件下进行,并且可以在连续流光反应器中进行。与间歇反应相比,使用连续流光反应器可显著缩短反应时间(间歇反应中0.04 mmol底物在4小时后实现完全转化,而在流光反应器中相同量的底物在40分钟内完全转化为产物)。该反应的机理研究表明,四氢呋喃不仅起到溶剂的作用,还是关键的氢和电子供体。

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