• Home
  • Search Results
  • Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes.

Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes.

Chemical & pharmaceutical bulletin (2013-10-04)
Kiyofumi Inamoto
ABSTRACT

Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Palladium, powder, <1 μm, ≥99.9% trace metals basis
Sigma-Aldrich
Palladium, powder, 99.995% trace metals basis
Sigma-Aldrich
Palladium black, surface area 40-60 m2/g, 99.95% trace metals basis
Sigma-Aldrich
Palladium, granular, 99.99% trace metals basis
Sigma-Aldrich
Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, wire, diam. 1.0 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, sponge, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 0.05 mm, 99.9% trace metals basis
Palladium, foil, 50x50mm, thickness 0.1mm, as rolled, 99.95%
Palladium, foil, 50x50mm, thickness 0.25mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, light tested, 50x50mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.004mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.005mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.006mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.008mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.0125mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, not light tested, 150x150mm, thickness 0.0125mm, 99.95%
Palladium, foil, not light tested, 150x150mm, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, not light tested, 150x150mm, thickness 0.02mm, as rolled, 99.95%
Palladium, foil, not light tested, 150x150mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, not light tested, 25x25mm, thickness 0.0005mm, 99.75%