title: Palladium-Catalyzed Direct α-Aryation of Benzyl Thioethers with Aryl Bromides.
abstract: The arylation of sp3-hybridized C-H's bonds is a powerful strategy to build molecular complexity and diversity. A novel and efficient palladium-catalyzed direct sp3C-H arylation of aryl and alkyl benzyl thioether derivatives with aryl bromides is reported. The reaction involves reversible deprotonation of the benzylic C-H's of the thioether with either LiN(SiMe3)2or NaN(SiMe3)2and subsequent cross-coupling to provide the functionalized products in up to 97% yield. A screen of 24 of the most successful ligands in cross-coupling chemistry led to the identification of NiXantPhos as the only viable ligand for this challenging coupling.
authors: P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, United States ; Departamento de Química, Universidade Federal do Paraná, CP 19081, 81531-990, Curitiba - PR, Brazil.
authors: Gustavo
authors: G
authors: Frensch
authors: P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, United States.
authors: Nusrah
authors: N
authors: Hussain
authors: Departamento de Química, Universidade Federal do Paraná, CP 19081, 81531-990, Curitiba - PR, Brazil.
authors: Francisco A
authors: FA
authors: Marques
authors: P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, United States.
authors: Patrick J
authors: PJ
authors: Walsh
keywords: Arylation; Cross-Coupling; C–H functionalization; Palladium; Sulfides