Nitrogen → 2-Vinylquinoline

Participants

Reaction Conditions

Reaction Steps

2-chloroquinoline (1-1) (1.00 g, 6.1 mmol) in toluene (25 mL) was sparged with N2 gas for 5 min, and tributyl(vinyl)stannane (2.52 g, 2.33 mL, 8.0 mmol) and tetrakis(triphenylphosphine)palladium (0.353 g, 0.31 mmol) were added. The mixture was heated at 125° C. for 1 h, then cooled and concentrated in vacuo. The residue was suspended in CH2Cl2 (20 mL) and purified by silica gel flash column chromatography (80 g cartridge), eluting with 0-30% EtOAc/hexanes over 20 min. The fractions containing the desired product (1-2) were pooled, and after solvent removal in vacuo, 700 mg (74%) of a clear oil were obtained. LC/MS: m/z (M+H)=156.0.

Provenance & Evidence