Simple Photo-Induced Trifluoromethylation of Aromatic Rings

被引：32

作者：

Egami, Hiromichi ^{[1
]}

Ito, Yuta ^{[1
]}

Ide, Takafumi ^{[1
]}

Masuda, Shuya ^{[1
]}

Hamashima, Yoshitaka ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka 4228526, Japan

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 15期

关键词：

trifluoromethylation; radical; photo-irradiation; Umemoto reagent; aromatic substitution; C-H TRIFLUOROMETHYLATION; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; CATALYZED TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; METAL-FREE; FLUORINE; ARENES; COPPER; REAGENT; AGENTS;

D O I：

10.1055/s-0037-1609759

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trifluoromethylation of various aromatic compounds with Umemoto reagent II (2,8-difluoro-5-(trifluoromethyl)-5 H -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.

引用

页码：2948 / 2953

页数：6

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