Visible-Light-Induced Trifluoromethylsulfonylation Reaction of Diazo Compounds Enabled by Manganese Catalysis
Jinrui Bai, Shijia Li, Dan Qi, Zhuoheng Song, Bin Li, Lin Guo, Lijuan Song, Wujiong Xia
Abstract
A visible-light-induced trifluoromethylsulfonylation reaction of diazo compounds is herein reported. This developed synthetic method captures the relatively rare trifluoromethyl sulfone radicals via coordination to the Mn(acac) 3 catalyst, delivering the corresponding α-trifluoromethyl sulfone esters in good to moderate yields (up to 82%). This protocol exhibits broad substrate scope and is easily carried out under mild reaction conditions. Furthermore, a plausible mechanism of the reaction was investigated through DFT calculations.
Topics & Concepts
DiazoChemistryTrifluoromethylManganeseSulfoneCatalysisRadicalSubstrate (aquarium)PhotochemistryReaction conditionsVisible spectrumReaction mechanismCombinatorial chemistryOrganic chemistryOptoelectronicsPhysicsOceanographyAlkylGeologyCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesFluorine in Organic Chemistry