Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF<sub>3</sub> Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols
Deng Zhu, Tong‐Mei Ding, Huiyun Luo, Hua Ke, Zhi‐Min Chen
Abstract
A selenium-catalyzed trifluoromethylthiolation/[2,3]-sigmatropic rearrangement of tertiary allylic and propargylic alcohols which could provide straightforward and facile access to trifluoromethyl sulfoxides was developed. Various allylic and allenic trifluoromethyl sulfoxides were obtained with moderate to excellent yields. Meanwhile, a Lewis acid mediated trifluoromethylthiolation/1,2-rearrangement to synthesize β-SCF3 carbonyl compounds was also accomplished. These two tandem reactions feature with mild reaction conditions and metal-free. During these two reactions, the chemoselectivity of electrophilic trifluoromethylthiolation was revealed.
Topics & Concepts
ChemistryAllylic rearrangementTrifluoromethylChemoselectivityElectrophileTandemLewis acids and basesMedicinal chemistryOrganic chemistryCombinatorial chemistryCatalysisAlkylComposite materialMaterials scienceFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsSulfur-Based Synthesis Techniques