B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Electron Donor–Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions
Wenkai Yuan, Jie Huang, Xin Xu, Long Wang, Xiang‐Ying Tang
Abstract
An efficient B(C6F5)3-catalyzed aerobic oxidative C–S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor–acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.
Topics & Concepts
ChemistryThiophenolCatalysisIndole testElectron acceptorElectron donorPhotochemistryAcceptorElectron transferMolecular oxygenVisible spectrumCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryOptoelectronicsPhysicsCondensed matter physicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods