Synthesis of amides using the Ritter reaction with bismuth triflate catalysis
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Typical procedure: synthesis of tert-butylbenzamide
tert-Butanol (77.4 μL, 0.8 mmol) was added with stirring to a solution of bismuth triflate (105 mg, 0.16 mmol) and benzonitrile (0.4 mL, 3.89 mmol) in water (0.2 mL). After 17 h at 100 °C, the mixture was cooled and poured into aqueous KOH solution (20% w:v; 5 mL) to neutralize the acid and precipitate the catalyst. The product was extracted with dichloromethane (2 × 5 mL) and the organic phase was filtered, rotary evaporated and chromatographed (cyclohexane:EtOAc 9:1 to 1:1) to afford tert-BuNHCOC6H5 (131
Acknowledgements
We thank GlaxoSmithKline for the generous endowment (to A.G.M.B.), the Royal Society and the Wolfson Foundation for a Royal Society Wolfson Research Merit Award (to A.G.M.B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medical Sciences at Imperial College London, the Engineering and Physical Sciences Research Council and GlaxoSmithKline for generous support of our studies, and the Thorpe Bequest for a studentship (to E.C.).
References and notes (12)
- et al.
Comb. Chem. High Throughput Screening
(2002) - et al.
Synthesis
(2003) - et al.
J. Am. Chem. Soc.
(1949)et al.J. Am. Chem. Soc.
(1948)et al.J. Org. React.
(1969) - et al.
J. Org. Chem.
(1981) - et al.
J. Chem. Soc., Chem. Commun.
(1973) - et al.
J. Org. Chem.
(1995)
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