Copper-Catalyzed Remote C(sp<sup>3</sup>)–H Phosphorothiolation of Sulfonamides and Carboxamides in a Multicomponent Reaction
Shanshan Shi, Pengbo Zhang, Chen Luo, Shaohua Zhuo, Yumeng Zhang, Guo Tang, Yufen Zhao
Abstract
The catalytic C(sp3)–H functionalization is highly desirable yet challenging in organic synthesis. Incorporation of the SP(O)(OR)2 group through C(sp3)–H functionalization remains unexplored. We herein report an unprecedented protocol for phosphorothiolation of primary and secondary C(sp3)–H via a multicomponent reaction with N-fluoro-substituted amides, elemental sulfur, and P(O)H compounds involving a sequence of amidyl radical generation, 1,5-HAT, and a Cu-catalyzed cross coupling of the resulting carbon radical with (RO)2P(O)SH (generated in situ).
Topics & Concepts
ChemistryCatalysisSurface modificationSulfurPrimary (astronomy)CopperCoupling reactionCombinatorial chemistryCarbon fibersMedicinal chemistryOrganic chemistryPhysical chemistryAstronomyPhysicsComposite numberComposite materialMaterials scienceCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions