Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides
Che-Ming Hsu, Shao‐Chi Lee, Hao-En Tsai, Yong‐Ting Tsao, Cheng-Lin Chan, Shinje Miñoza, Zong‐Nan Tsai, Liyun Li, Hsuan‐Hung Liao
Abstract
The C–S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C–S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.
Topics & Concepts
ArylHalideCatalysisChemistryCoupling (piping)Coupling reactionMedicinal chemistryOrganic chemistryMaterials scienceMetallurgyAlkylAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling ReactionsChemical Synthesis and Reactions