Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization domino approach.
[reaction: see text] In a convenient one-pot process, easily accessed propargyl vinyl ethers and aromatic amines are effectively converted into tetra- and pentasubstituted 5-methylpyrroles which can further be transformed into 5-formylpyrroles via IBX-mediated oxidation. The cascade reaction proceeds through a silver(I)-catalyzed propargyl-Claisen rearrangement, an amine condensation, and a gold(I)-catalyzed 5-exo-dig heterocyclization.
Binder
Jörg T
JT
Department Chemie, Technische Universität München, Garching, Germany.
Kirsch
Stefan F
SF