| Abstract
| - 2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst.Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladiumcatalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylideneacetone) and BINAP (2,2‘-bis(diphenylphosphino)-1,1‘-binaphthalene). Although the intermoleculararylation of amides is less general than that reported previously for ketones, unfunctionalized andelectron-rich aryl halides gave α-arylamides in 48−75% yield and N-methyl-α-phenylpyrrolidinonein 49% yield. These reactions provided the highest yields yet reported for regioselective amidearylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52−82% yield.Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use ofdioxane, rather than THF, solvent was important for some of the amide arylations.
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