One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis

被引:102
作者
Carboni, Aude [1 ]
Dagousset, Guillaume [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, UMR 8180, Inst Lavoisier Versailles, F-78035 Versailles, France
关键词
VISIBLE-LIGHT PHOTOCATALYSIS; C-H TRIFLUOROMETHYLATION; CHIRAL PHOSPHORIC-ACID; BOND FORMATION; ELECTROPHILIC TRIFLUOROMETHYLATION; SODIUM TRIFLUOROMETHANESULFINATE; MEDIATED TRIFLUOROMETHYLATION; UNACTIVATED ALKENES; ORGANIC-SYNTHESIS; CONSTRUCTION;
D O I
10.1039/c4cc07066f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report herein the first photoredox-catalyzed intermolecular aryl- and heteroaryltrifluoromethylation of alkenes. Under the optimized conditions using Umemoto's reagent as a CF3 source, a wide range of styrenes can be readily difunctionalized, affording the corresponding trifluoromethylated adducts in up to 99% yield.
引用
收藏
页码:14197 / 14200
页数:4
相关论文
共 27 条
[21]   One-pot efficient synthesis of β-aryl-β-sulfanyl ketones via a four-component reaction of alkyl halides, thiourea benzaldehydes and acetophenones [J].
Abbasi, Mohammad ;
Nowrouzi, Najmeh ;
Mousavi, Saadat .
TETRAHEDRON LETTERS, 2020, 61 (09)
[22]   One-Pot Three-Component Highly Selective Synthesis of Homoallylboronates by Using Metal-Free Catalysis [J].
Ibrahem, Ismail ;
Breistein, Palle ;
Cordova, Armando .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5175-5179
[23]   Sequential Asymmetric Catalysis in Michael-Michael-Michael-Aldol Reactions: Merging Organocatalysis with Photoredox Catalysis in a One-Pot Enantioselective Synthesis of Highly Functionalized Decalines Bearing a Quaternary Carbon Stereocenter [J].
Hong, Bor-Cherng ;
Lin, Cheng-Wei ;
Liao, Wei-Kai ;
Lee, Gene-Hsiang .
ORGANIC LETTERS, 2013, 15 (24) :6258-6261
[24]   Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence [J].
Sureshbabu, Radhakrishnan ;
Saravanan, Velu ;
Dhayalan, Vasudevan ;
Mohanakrishnan, Arasambattu K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) :922-935
[25]   Chemo selective one-pot synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using Amberlite IR-120 [J].
Nile, Shivraj Hariram ;
Kumar, Brajesh ;
Park, Se Won .
ARABIAN JOURNAL OF CHEMISTRY, 2015, 8 (05) :685-691
[26]   Ultrasound-Assisted Expedient and Green Synthesis of a New Series of Diversely Functionalized 7-Aryl/heteroarylchromeno[4,3-d]pyrido[1,2-a]pyrimidin-6(7H)-ones via One-Pot Multicomponent Reaction under Sulfamic Acid Catalysis at Ambient Conditions [J].
Brahmachari, Goutam ;
Karmakar, Indrajit ;
Nurjamal, Khondekar .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (08) :11018-11028
[27]   Ultrasound-Promoted Expedient and Green Synthesis of Diversely Functionalized 6-Amino-5-((4-hydroxy-2-oxo-2H-chromen-3-yl)(aryl)methyl)pyrimidine-2,4(1H,3H)-diones via One-Pot Multicomponent Reaction under Sulfamic Acid Catalysis at Ambient Conditions [J].
Brahmachari, Goutam ;
Mandal, Mullicka ;
Karmakar, Indrajit ;
Nurjamal, Khondekar ;
Mandal, Bhagirath .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (06) :6369-6380