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 sp³ C-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)₂ or NaN(SiMe₃)₂ and 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.

SUBMITTER: Frensch G 

PROVIDER: S-EPMC4323356 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature