A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

ABSTRACT: An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indole-based phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pK_a up to 35) were reversibly depotonated by LiO ^t Bu, NaO ^t Bu, or NaN(SiMe₃)₂.

SUBMITTER: Zheng B 

PROVIDER: S-EPMC3994175 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature