Chemo‑, Regio‑, and Stereoselective Trifluoromethylation of Styrenes via Visible Light-Driven Single-Electron Transfer (SET) and Triplet–Triplet Energy Transfer (TTET) Processes

A process for tunable and chemo-, regio-, and stereoselective photocatalytic trifluoromethylation of styrenes was developed. Thermodynamically stable E-trifluoromethylated alkenes were prepared using Togni’s reagent in the presence of Ru(bpy)3Cl2·6H2O under visible light irradiation, whereas less th...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 21; pp. 10434 - 10446
Main Authors Lin, Qing-Yu, Xu, Xiu-Hua, Qing, Feng-Ling
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.11.2014
Amer Chemical Soc
Subjects
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Electron Transport
Electrons
Hydrocarbons, Fluorinated
Iridium - chemistry
Light
Methylation
Molecular Structure
Physical Sciences
Ruthenium - chemistry
Science & Technology
Stereoisomerism
Styrenes - chemical synthesis
Styrenes - chemistry
3-COMPONENT OXYTRIFLUOROMETHYLATION
OLEFINIC TRIFLUOROMETHYLATION
ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS
COPPER-CATALYZED TRIFLUOROMETHYLATION
MEDIATED TRIFLUOROMETHYLATION
BETA-TRIFLUOROMETHYLSTYRENES
RADICAL TRIFLUOROMETHYLATION
OXIDATIVE TRIFLUOROMETHYLATION
C-H TRIFLUOROMETHYLATION
PHOTOREDOX CATALYSIS
Online AccessGet full text

Cover

More Information
Summary:A process for tunable and chemo-, regio-, and stereoselective photocatalytic trifluoromethylation of styrenes was developed. Thermodynamically stable E-trifluoromethylated alkenes were prepared using Togni’s reagent in the presence of Ru(bpy)3Cl2·6H2O under visible light irradiation, whereas less thermodynamically stable Z-trifluoromethylated alkenes were obtained by employing Umemoto’s reagent and photocatalyst Ir(ppy)3.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502040t