Visible-light mediated trifluoromethylation of p-quinone methides by 1,6-conjugate addition using pyrylium salt as organic photocatalyst

被引：29
作者：
Ghosh, Krishna Gopal [1 ]
Chandu, Palasetty [1 ]
Mondal, Santanu [2 ]
Sureshkumar, Devarajulu [1 ]
机构：
[1] Indian Inst Sci Educ & Res Kolkata Mohanpur, Dept Chem Sci, Mohanpur 741246, W Bengal, India
[2] OIST, 1919-1 Tancha, Onna Son, Okinawa, Japan
来源：
TETRAHEDRON | 2019年 / 75卷 / 33期
关键词：
Trifloromethylation; Photoredox catalysis; p-Quinone methides (p-QMs); 1,6-Conjugate addition; Organocatalysis; PHOTOREDOX-CATALYZED TRIFLUOROMETHYLATION; EXPEDIENT ACCESS; FACILE SYNTHESIS; FLUORINE; ALKENES; PHARMACEUTICALS; CYCLIZATION; GENERATION; HYDROTRIFLUOROMETHYLATION; ADDITION/AROMATIZATION;
D O I：
10.1016/j.tet.2019.06.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A transition metal free visible light mediated organo photoredox catalyzed trifluoromethylation of p-quinone methides (p-QMs) to construct fluoro-analogs of dichlorodiphenyltrichloroethane (DDT) is reported using a bench stable, inexpensive Langlois reagent as a trifluoromethyl radical source. This protocol could generate a benzylic C(sp(3))-CF3 bond with excellent yield under mild reaction conditions using 1,6-conjugate addition/aromatization of trifluoromethyl radical in the absence of any external additives. Further, we demonstrate di-trifluoromethylation and gram scale synthesis of this reaction. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4471 / 4478
页数：8
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