Related Experiment Video
Updated: Jan 19, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Ir(III)-Catalyzed Mono-Olefination of Aryl C-H Bonds Using -SCF3 as a Weak Directing Group
Rui-Peng Bao1, Xian Chen2, Chen Li2
1CAS Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences , Shanghai Institute of Organic Chemistry , CAS. 345 Lingling Road , Shanghai 200032 , China.
Abstract:
The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2'-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Nucleophilic Aromatic Substitution: Elimination–Addition
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

