jo6b00488_si_001.pdf (513.21 kB)
One-Pot Amide Bond Formation from Aldehydes and Amines via a Photoorganocatalytic Activation of Aldehydes
journal contribution
posted on 2016-05-26, 00:00 authored by Giorgos
N. Papadopoulos, Christoforos G. KokotosA mild,
one-pot, and environmentally friendly synthesis of amides
from aldehydes and amines is described. Initially, a photoorganocatalytic
reaction of aldehydes with di-isopropyl azodicarboxylate leads to
an intermediate carbonyl imide, which can react with a variety of
amines to afford the desired amides. The initial visible light-mediated
activation of a variety of monosubstituted or disubstituted aldehydes
is usually fast, occurring in a few hours. Following the photocatalytic
reaction, addition of the primary amine at room temperature or the
secondary amine at elevated temperatures leads to the corresponding
amide from moderate to excellent yields without epimerization. This
methodology was applied in the synthesis of Moclobemide, a drug against
depression and social anxiety.