Rapid Trifluoromethylation and Perfluoroalkylation of Five-Membered Heterocycles by Photoredox Catalysis in Continuous Flow

被引：144

作者：

Straathof, Natan J. W. ^{[1
]}

Gemoets, Hannes P. L. ^{[1
]}

Wang, Xiao ^{[2
,3
]}

Schouten, Jaap C. ^{[1
]}

Hessel, Volker ^{[1
]}

Noel, Timothy ^{[1
,4
]}

机构：

[1] Eindhoven Univ Technol, Dept Chem Engn & Chem, NL-5612 AZ Eindhoven, Netherlands

[2] Harvard Univ, Sch Med, Harvard NeuroDiscovery Ctr, Cambridge, MA 02139 USA

[3] Brigham & Womens Hosp, Cambridge, MA 02139 USA

[4] Univ Ghent, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

CHEMSUSCHEM | 2014年 / 7卷 / 06期

基金：

欧洲研究理事会;

关键词：

flow chemistry; heterocycles; homogeneous catalysis; photochemistry; ruthenium; LIGHT; ALKENES; BATCH; TECHNOLOGY; CHEMISTRY; FLUORINE; ARENES; MILD;

D O I：

10.1002/cssc.201301282

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Trifluoromethylated and perfluoroalkylated heterocycles are important building blocks for the synthesis of numerous pharmaceutical products, agrochemicals and are widely applied in material sciences. To date, trifluoromethylated and perfluoroalkylated hetero-aromatic systems can be prepared utilizing visible light photoredox catalysis methodologies in batch. While several limitations are associated with these batch protocols, the application of microflow technology could greatly enhance and intensify these reactions. A simple and straightforward photocatalytic trifluoromethylation and perfluoroalkylation method has been developed in continuous microflow, using commercially available photocatalysts and microflow components. A selection of five-membered hetero-aromatics were successfully trifluoromethylated (12examples) and perfluoroalkylated (5examples) within several minutes (8-20min).

引用

页码：1612 / 1617

页数：6

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