Carbene-Catalyzed Redox Amidations
2007; Georg Thieme Verlag; Volume: 2008; Issue: 01 Linguagem: Inglês
10.1055/s-2007-991416
ISSN1861-1958
Autores Tópico(s)Catalytic Cross-Coupling Reactions
ResumoRovis and co-worker report a carbene-catalyzed internal redox process providing a direct route from α-reducible aldehydes 1 and amines 2 to α-reduced amides 3. Carbene precursor 4 is used for the in situ carbene formation. Cocatalyst 1-hydroxy-7-azabenzotriazole 5 (HOAt) generates activated esters 6 which undergo in situ amidation, thereby regenerating carbene 7. α,α-Dichloro aldehydes, α,β-epoxy aldehydes, α,β-aziridino aldehydes and enals as α-reducible aldehyde component lead to α-chloro amides, β-hydroxy amides, β-amino amides and alkanamides. With some of these substrates a waste-free amidation is realized.
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