Interrupting the Barton–McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of <i>O</i>-Alkyl Thiocarbonates
Liu Zhi-yun, Silas P. Cook
Abstract
The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.
Topics & Concepts
TrifluoromethylationChemistryAlkeneAlkyneAlkylOrganic chemistryCombinatorial chemistryMedicinal chemistryPhotochemistryTrifluoromethylCatalysisFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsSulfur-Based Synthesis Techniques