Categories: C=N Bond Formation >
Synthesis of imines
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Name Reactions
Recent Literature
Neat non-volatile amines react efficiently with various aromatic aldehydes
in the absence of any catalyst or solvent, to give imines after a reaction
time of eight minutes under microwave irradiation. 1,3-dimethylurea
dispersed on montmorillonite K10 is used as an methylamine precursor.
L. Paquin, J. Hamelin, F. Texier-Boullet, Synthesis, 2006, 1635-1638.
Manganese dioxide is employed as an in situ oxidant for the one-pot conversion
of alcohols into imines. In combination with polymer-supported cyanoborohydride
(PSCBH), a one-pot oxidation-imine formation-reduction sequence enables alcohols
to be converted directly into both secondary and tertiary amines.
L. Blackburn, R. J. K. Taylor, Org. Lett., 2001,
3, 1637-1639.
An intermolecular reductive Schiff base formation from nitroarenes and
benzaldehydes to yield diarylimines is carried out in the presence of iron
powder and dilute acid. This process tolerates various functional groups and
often proceeds quantitatively with no need for purification.
A. L. Korich, T. S. Hughes, Synlett, 2007,
2602-2604.
By employing Pd(OAc)2 and (t-Bu)2PNP(i-BuNCH2CH2)3N
as ligand, a broad range of aryl bromides and chlorides possessing
base-sensitive substituents provide coupling products with bulky aryl amines in
good to excellent yields. An efficient coupling of vinyl bromides with a variety
of amines produces imines and enamines at room temperature.
Ch. V. Reddy, J. V. Kingston, J. G. Verkade, J. Org. Chem., 2008,
73, 3047-3062.
A high-yielding, asymmetric synthesis of novel 4-formyl-1-(2- and
3-haloalkyl)azetidin-2-ones was developed as valuable starting materials for the
synthesis of different enantiomerically enriched bicyclic azetidin-2-ones, such
as piperazine, morpholine, and 1,4-diazepane annulated β-lactam derivatives.
W. Van Brabandt, M. Vanwalleghem, M. D'hooghe, N. De Kimpe, J. Org. Chem., 2006, 71, 7083-7086.
Readily available and stable titanocene-alkyne complexes can be used for the
hydroamination of internal and terminal alkynes. The reactions of terminal alkynes with aliphatic amines proceed highly
selectively to give the corresponding primary anti-Markovnikov functionalized
imines in good to excellent yields.
A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew. Chem. Int. Ed.,
2002, 41, 2541-2543.
A number of new reactions of IBX with heteroatom-containing substrates were
discovered and their utility was demonstrated. IBX was used for the generation
of imines from secondary amines in notably high yields, for the oxidative
aromatization of nitrogen heterocycles and for the cleavage of dithianes.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew.
Chem., 2003, 115, 4211-4216.
[RuCl2(CO)3]2/dppp is a highly effective
catalyst system for the intramolecular oxidative amination of various
aminoalkenes in presence of K2CO3 and allyl acetate in
N-methylpiperidine to give the corresponding cyclic imines and
indoles in excellent yields.
T. Kondo, T. Okada, T.-A. Mitsudo, J. Am. Chem. Soc., 2002, 124,
186-187.
The reaction of aldehydes, amines, and TMSCN in the presence of 2-iodoxybenzoic
acid (IBX) and tetrabutylammonium bromide (TBAB) afforded α-iminonitriles in
good to excellent yields under mild conditions. The presence of TBAB is
essential for this transformation.
P. Fontaine, A. Chiaroni, G. Masson, J. Zhu, Org. Lett., 2008,
10, 1509-1512.
