简单光诱导芳香环三氟甲基化

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Synthesis-Stuttgart Pub Date : 2018-06-26 DOI:10.1055/s-0037-1609759

H. Egami, Yuta Ito, Takafumi Ide, Shuya Masuda, Y. Hamashima

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引用次数: 20

摘要

摘要用Umemoto试剂II(2,8-二氟-5-(三氟甲基)- 5h -二苯并[b,d]噻吩-5-三氟酸铵)在简单的光照射条件下以中高收率进行了各种芳香化合物的三氟甲基化，无需任何催化剂、添加剂或活化剂。紫外可见光谱和核磁共振光谱分析表明，在三氟甲基化试剂和底物之间预先形成电子供体-受体络合物，如先前的研究所提出的，对于三氟甲基自由基的生成并不必要。相反，自由基似乎是由Umemoto试剂的简单光活化形成的。

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Simple Photo-Induced Trifluoromethylation of Aromatic Rings

Abstract The trifluoromethylation of various aromatic compounds with Umemoto reagent II (2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium triflate) proceeded in moderate to good yields under simple photo-irradiation conditions without any catalyst, additive, or activator. UV-Vis and NMR spectral analyses indicated that pre-formation of an electron donor-acceptor complex between the trifluoromethylating reagent and the substrate, as proposed in previous studies, is not essential for generation of the trifluoromethyl radical. Instead, the radical appears to be formed by simple photo-activation of the Umemoto reagent.

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来源期刊

Synthesis-Stuttgart 化学-有机化学

CiteScore

4.50

自引率

7.70%

发文量

435

审稿时长

1 months

期刊介绍： SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.