Rapid Access to 3-Substituted Pyridines and Carbolines via a Domino, Copper-free, Palladium-Catalyzed Sonogashira Cross-Coupling/6π-Aza Cyclization Sequence

J Org Chem. 2021 Dec 17;86(24):17748-17761. doi: 10.1021/acs.joc.1c02034. Epub 2021 Nov 30.

Abstract

Herein, we report a one-pot, three-component method for the preparation of 3-substituted pyridines and carbolines via copper-free, palladium-catalyzed Sonogashira cross-coupling with aryl iodides, followed by 6π-aza cyclization. This arylation cross-coupling/annulation cascade provides easy access to substituted, fused pyridines from readily available substrates in good yields (67-92%) with complete selectivity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbolines*
  • Catalysis
  • Cyclization
  • Palladium*
  • Pyridines

Substances

  • Carbolines
  • Pyridines
  • Palladium