Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization

Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization

We report a new synthesis of phenanthridines based on palladium-catalyzed picolinamide-directed sequential C-H functionalization reactions starting from readily available benzylamine and aryl iodide precursors. Under the catalysis of Pd(OAc)2, the ortho-C-H bond of benzylpicolinamides is first arylated with an aryl iodide. The resulting biaryl compound is then subjected to palladium-catalyzed p...

Palladium-catalyzed synthesis of cyclopentane-fused benzocyclobutenes via tandem directed carbopalladation/C-H bond functionalization.

A new Pd-catalyzed reaction for the stereoselective synthesis of cyclopentane-fused benzocyclobutenes is described. These transformations likely proceed via carbamate-directed carbopalladation followed by intramolecular C-H activation of an alkylpalladium intermediate. The mechanistic relationship between these transformations and Pd-catalyzed reactions of gamma-(n-Boc-amino)alkenes with aryl b...

Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines

A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp(2))-H bonds of γ-arylpropylamine substrates is reported. This reaction proceeds selectively with a variety of γ-arylpropylamines bearing strongly electron-donating or withdrawing substituents, complementing our previously reported PA-directed electrophilic aromatic substitution approach to this transformati...

Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

We have examined the direct arylation of imidazolinone (1) with 6 different palladium sources, 15 different phosphine ligands, 12 different bases and 14 different solvent systems. There is no significant difference between using Pd(OAc)2 and Pd(TFA)2. This reaction proceeds less efficiently or reproducibly with Pd2(dba)3/(o-biphenyl)PCy2, O=PCy3, O=PPh3, P(OMe)3, PCy3·HBF4, PCy3, PPBu /DMF, NMP...

Synthesis of heterocycles via palladium-catalyzed carbonylations.