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Reduction of amides to imines
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Recent Literature
A chemoselective activation of a secondary amide with triflic anhydride in the
presence of 2-fluoropyridine enables a mild reduction using triethylsilane, a
cheap and rather inert reagent. Imines can be isolated after a basic workup or
readily transformed to the aldehydes following an acidic workup. The amine
moiety can be accessed by addition of Hantzsch ester to the reaction mixture.
G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc., 2010,
132, 12817-12819.
Zirconocene hydride catalyzes a mild method for the semireduction of both
secondary and tertiary amides to imines. While secondary amides furnish a
diverse array of imines in very good yield with excellent chemoselectivity, a
reductive transamination of tertiary amides is also achievable in the presence
of a primary amine at room temperature.
R. A. Kehner, G. Zhang, L. Bayeh-Romero, J. Am. Chem. Soc.,
2023, 145, 4921-4927.
Zirconocene hydride catalyzes a mild method for the semireduction of both
secondary and tertiary amides to imines. While secondary amides furnish a
diverse array of imines in very good yield with excellent chemoselectivity, a
reductive transamination of tertiary amides is also achievable in the presence
of a primary amine at room temperature.
R. A. Kehner, G. Zhang, L. Bayeh-Romero, J. Am. Chem. Soc.,
2023, 145, 4921-4927.
Related
A transition-metal-free catalytic hydrosilylation based on t-BuOK (5 mol
%) and (MeO)3SiH or (EtO)3SiH allows the reduction of
tertiary amides to their corresponding enamines with high selectivity in very
good yields.
A. Volkov, F. Tinnis, H. Adolfsson, Org. Lett., 2014,
16, 680-683.