Electrochemical Cross-Coupling of P(O)-H with Thioesters: Green Synthesis of Phosphorothioates
Lihua Huang, Fanhua Meng, Wenying Guo, Xiandong Dai, Zirui Lv, Pingping Tang, Yongbiao Guo, Chunru Cheng, Zhenhua Gao
Abstract
An efficient and eco-friendly electrochemical strategy enables the metal-, base-, and oxidant-free cross-coupling between thioesters and P(O)-H species for the construction of P-S bonds. The reaction proceeds under mild conditions and has a broad substrate scope (61 examples, up to 95%). Even in gram-scale synthesis, satisfactory yields can be achieved. The utilization of thioesters circumvents traditional procedures that involve gaseous short-chain alkyl thiols. Meanwhile, it offers a practical alternative to malodorous and unstable thiols.
Topics & Concepts
ChemistryElectrochemistrySubstrate (aquarium)AlkylCombinatorial chemistryScope (computer science)Reaction conditionsGreen chemistryOrganic chemistryNanotechnologyCatalysisSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods