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

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 91期

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

页码：14197 / 14200

页数：4

共 93 条

[1] Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
Alix, Aurelien
Lalli, Claudia
Retailleau, Pascal
Masson, Geraldine
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10389 - 10392
[2] [Anonymous], CHEM HETEROCYCLIC CO
[3] Metal-Free Dioxygenation of Enecarbamates Mediated by a Hypervalent Iodine Reagent
Bekkaye, Mathieu
Su, Yingpeng
Masson, Geraldine
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (19) : 3978 - 3982
[4] Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895
[5] Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates
Carboni, Aude
Dagousset, Guillaume
Magnier, Emmanuel
Masson, Geraldine
[J]. ORGANIC LETTERS, 2014, 16 (04) : 1240 - 1243
[6] Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]
[7] Vaccinia Virus Virulence Factor N1L is a Novel Promising Target for Antiviral Therapeutic Intervention
Cheltsov, Anton V.
Aoyagi, Mika
Aleshin, Alexander
Yu, Eric Chi-Wang
Gilliland, Taylor
Zhai, Dayong
Bobkov, Andrey A.
Reed, John C.
Liddington, Robert C.
Abagyan, Ruben
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (10) : 3899 - 3906
[8] Chen P., 2013, SYNTHESIS-STUTTGART, P2919
[9] Copper-Catalyzed Tandem Trifluoromethylation/Semipinacol Rearrangement of Allylic Alcohols
Chen, Zhi-Min
Bai, Wei
Wang, Shao-Hua
Yang, Bin-Miao
Tu, Yong-Qiang
Zhang, Fu-Min
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9781 - 9785
[10] Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction
Courant, Thibaut
Masson, Geraldine
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) : 423 - 427

← 1 2 3 4 5 6 7 8 9 10 →