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DOI: 10.1055/s-0029-1219784
Indium-Catalyzed N-Formylation of Amines under Solvent-Free Conditions
Publication History
Publication Date:
23 March 2010 (online)
Abstract
We have developed a simple, mild method for N-formylation of a wide variety of amines in the presence of indium metal as a catalyst under solvent-free conditions. This reaction is applicable to the chemoselective N-formylation of amino groups and α-amino acid esters without epimerization.
Key words
amine - formylation - formic acid - indium - ethanolamine - formylamino ester - solvent-free
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References and Notes
Typical procedure for the formylation of amines: A mixture of amine (2 mmol), formic acid (purity = 99%; 226 µL, 6 mmol), and In metal (23 mg, 0.2 mmol) was stirred at 70 ˚C, and the reaction was monitored by TLC. After completion of the reaction, the mixture was diluted with CH2Cl2 and filtered through Celite. The filtrate was washed with saturated NaHCO3 and brine, then dried over anhydrous MgSO4. After filtration and evaporation of the solvent, the residue was purified by column chromatography on silica gel to give the formylated product.