Radical Perfluoroalkylation Enabled by a Catalytically Generated Halogen Bonding Complex and Visible Light Irradiation
Radical Perfluoroalkylation Enabled by a Catalytically Generated Halogen Bonding Complex and Visible Light Irradiation
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催化生成的卤素键配合物和可见光照射实现自由基全氟烷基化
DOI：
10.1021/acs.orglett.1c04139
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Pitre, Spencer P.
中科院分区：
文献类型：
--
作者：
Tasnim, Tarannum;Ryan, Calvin;Christensen, Miranda L.;Fennell, Christopher J.;Pitre, Spencer P.
在可见光促进的单电子氧化还原反应中开发电荷转移络合物是开辟新的合成途径的一条很有前途的途径，而催化形成络合物的方法是促进这一化学过程的关键。本报告描述了使用取代的对苯二酚催化剂来促进自由基全氟烷基化反应。机理研究表明，该反应是通过在对苯二酚催化剂和全氟烷基卤化物自由基前驱体之间形成可见光吸收的卤素键合络合物来引发的。
Exploiting charge-transfer complexes in visible light-promoted single-electron redox reactions is a promising route for opening novel synthetic pathways, and catalytic approaches to complex formation are critical for facilitating this chemistry. This report describes the use of a substituted hydroquinone catalyst to promote radical perfluoroalkylation reactions. Mechanistic studies indicate that the reaction is initiated through formation of a visible light-absorbing halogen bonding complex between the hydroquinone catalyst and the perfluoroalkyl halide radical precursor.