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Ir(I)-catalyzed synthesis of N-substituted pyridones from 2-alkoxypyridines via C-O bond cleavage.

Organic letters (2013-04-02)
Shiguang Pan, Naoto Ryu, Takanori Shibata
ABSTRACT

A cationic Ir(I) complex-catalyzed O-to-N-alkyl migration in 2-alkoxypyridines bearing a secondary alkyl group on the oxygen atom by C-O bond cleavage is described. The present transformation gave various N-alkylpyridones in moderate to good yields. The addition of sodium acetate played a key role in suppressing β-hydrogen elimination.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Iridium, powder, 99.9% trace metals basis
Sigma-Aldrich
Iridium, wire, diam. 0.15 mm, 99.9% trace metals basis
Sigma-Aldrich
Iridium, evaporation slug, diam. × L 0.6 cm × 1.2 cm, 99.9% trace metals basis
Sigma-Aldrich
Iridium, black, powder, −200 mesh, ≥99% trace metals basis
Sigma-Aldrich
Iridium, foil, thickness 0.25 mm, 99.9% trace metals basis