Efficient Carbonylation of Aryl and Heteroaryl Bromides under Atmospheric Pressure of CO

Abstract

In the presence of Et₃N and n-BuOH, efficient alkoxycarbonylation of (hetero)aromatic bromides was achieved under atmospheric pressure of carbon monoxide with in situ generated palladium/rac-BINAP as catalyst.

Key words

palladium catalyst - cross-coupling - atmospheric pressure - carbonylation - alkoxycarbonylation

References and Notes

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15

Representative Procedure A stirred solution of 7-bromoisoquinoline (62 mg, 0.3 mmol) and Et₃N (0.07 mL, 0.45 mmol) in n-BuOH (1 mL) was treated with PdCl₂ (1 mg, 2 mol%) and rac-BINAP (7 mg, 4 mol%). The reaction mixture was degassed and refilled with CO (balloon) for three times, and then stirred for 12 h at 120 ˚C. Solvent was removed under reduced pressure, and the resulting residue was purified by column chromatography to provide butyl isoquinoline-7-carboxylate in 96% yield (66 mg).