Photoredox-Induced Three-Component Azido- and Aminotrifluoromethylation of Alkenes

被引：179

作者：

Dagousset, Guillaume ^{[1
]}

Carboni, Aude ^{[1
]}

Magnier, Emmanuel ^{[2
]}

Masson, Geraldine ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Univ Versailles St Quentin, Inst Lavoisier Versailles, UMR 8180, F-78035 Versailles, France

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 16期

关键词：

VISIBLE-LIGHT PHOTOCATALYSIS; COPPER-CATALYZED TRIFLUOROMETHYLATION; CHIRAL PHOSPHORIC-ACID; SODIUM TRIFLUOROMETHANESULFINATE; MEDIATED TRIFLUOROMETHYLATION; ASYMMETRIC-SYNTHESIS; UNACTIVATED ALKENES; BOND FORMATION; EFFICIENT; HYDROTRIFLUOROMETHYLATION;

D O I：

10.1021/ol5021477

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein a photoredox-catalyzed azidotrifluoromethylation of alkenes. Under the optimized conditions using [Ru(bpy)(3)(PF6)(2)] as the photocatalyst and Umemoto's reagent as the CF3 source, a wide range of substituted styrenes as well as various activated and non-activated alkenes can readily be difunctionalized, affording beta-trifluoromethylated azides or amines in good yields.

引用

页码：4340 / 4343

页数：4

共 75 条

[11] Trifluoromethylation of Alkenes with Concomitant Introduction of Additional Functional Groups
Egami, Hiromichi
Sodeoka, Mikiko
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) : 8294 - 8308
[12] Concise synthesis of oxindole derivatives bearing a 3-trifluoroethyl group: Copper-catalyzed trifluoromethylation of acryloanilides
Egami, Hiromichi
Shimizu, Ryo
Sodeoka, Mikiko
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 : 51 - 55
[13] Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group
Egami, Hiromichi
Shimizu, Ryo
Usui, Yoshihiko
Sodeoka, Mikiko
[J]. CHEMICAL COMMUNICATIONS, 2013, 49 (66) : 7346 - 7348
[14] Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines
Egami, Hiromichi
Kawamura, Shintaro
Miyazaki, Ayako
Sodeoka, Mikiko
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) : 7841 - 7844
[15] Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles
Egami, Hiromichi
Shimizu, Ryo
Kawamura, Shintaro
Sodeoka, Mikiko
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) : 4000 - 4003
[16] Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions
Egami, Hiromichi
Shimizu, Ryo
Sodeoka, Mikiko
[J]. TETRAHEDRON LETTERS, 2012, 53 (41) : 5503 - 5506
[17] Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature
Feng, Chao
Loh, Teck-Peng
[J]. CHEMICAL SCIENCE, 2012, 3 (12) : 3458 - 3462
[18] Iodotrifluoromethylation of Alkenes and Alkynes with Sodium Trifluoromethanesulfinate and Iodine Pentoxide
Hang, Zhaojia
Li, Zejiang
Liu, Zhong-Quan
[J]. ORGANIC LETTERS, 2014, 16 (14) : 3648 - 3651
[19] Highly Enantioselective Aza-Diels-Alder Reaction of 1-Azadienes with Enecarbamates Catalyzed by Chiral Phosphoric Acids
He, Long
Laurent, Gregory
Retailleau, Pascal
Folleas, Benoit
Brayer, Jean-Louis
Masson, Geraldine
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (42) : 11088 - 11091
[20] Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes
He, Yu-Tao
Li, Lian-Hua
Yang, Yan-Fang
Zhou, Zhao-Zhao
Hua, Hui-Liang
Liu, Xue-Yuan
Liang, Yong-Min
[J]. ORGANIC LETTERS, 2014, 16 (01) : 270 - 273

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