Trifluoromethyl Sulfoxides: Reagents for Metal‐Free C−H Trifluoromethylthiolation
Dong Wang, C. Grace Carlton, Masanori Tayu, Joseph J. W. McDouall, Gregory J. P. Perry, David J. Procter
Abstract
Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C-H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism.
Topics & Concepts
SulfoniumReagentChemistryTrifluoromethylSalt (chemistry)Combinatorial chemistryLigand (biochemistry)Surface modificationMetalOrganic chemistryPolymer chemistryReceptorBiochemistryPhysical chemistryAlkylFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesCyclopropane Reaction Mechanisms