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DOI: 10.1055/s-2008-1078218
A Mild and Clean Method for Oxidative Formation of Amides from Aldehydes and Amines
Publikationsverlauf
Publikationsdatum:
22. August 2008 (online)
Abstract
A metal-free direct oxidative formation of amides from aldehydes and amines using a hypervalent iodine(III) reagent or an ion-supported hypervalent iodine(III) reagent as a recyclable oxidant under mild conditions is reported.
Key words
(diacetoxyiodo)benzene - ion-supported hypervalent iodine(III) reagent - direct oxidative formation of amides - amines - aldehydes
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- 1
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References and Notes
All reagents and solvents were pure
analytical grade materials purchased from commercial sources and
were used without further purification, if not stated otherwise.
All melting points are uncorrected. The NMR spectra were recorded
in CDCl3 on a Bruker Avance 400 MHz instrument with TMS
as internal standard. TLC was carried out with 0.2 mm thick silica
gel plates (GF254). The columns were hand packed with silica gel
60 (200-300 µm). All products were confirmed by ¹H
NMR and ¹³C NMR. Unknown compounds were
additionally confirmed by elemental analysis.
Typical Procedure for the Oxidative Amidation
of Aldehydes with Amines by DIB: A solution of aldehyde (0.50
mmol, 1.0 equiv), DIB (0.75 mmol, 1.5 equiv), and two drops of H2O
in CHCl3 (1 mL) was cooled to 0 ˚C under an
inert atmosphere (N2) and the amine (0.65 mmol, 1.3 equiv)
was slowly added (about one drop in 1 h for 3 h). The reaction vessel
was capped and the reaction mixture was stirred for 3 h at 0 ˚C
and then for 17 h at r.t. The crude reaction mixture was purified
by column chromatography on silica gel (EtOAc-hexane, 1:4).
3,4,5-Trimethoxy-
N
-propylbenzamide
(Table 2, entry 9): white solid; mp 108 ˚C. ¹H
NMR (400 MHz, CDCl3): δ = 7.00 (s,
2 H), 6.25 (br, 1 H), 3.89 (s, 6 H), 3.87 (s, 3 H), 3.40 (q, J = 6.8 Hz, 2 H), 1.60-1.69
(m, 2 H), 0.98 (t, J = 8.0 Hz, 3
H). ¹³C NMR (100 MHz, CDCl3): δ = 167.3,
153.1, 140.7, 130.3, 104.3, 60.8, 56.2, 41.8, 22.9, 11.4. Anal.
Calcd for C13H19NO4: C, 61.64;
H, 7.56; N, 5.53; O, 25.27. Found: C, 61.60; H, 7.65; N, 5.60.
The ionic liquid [dibmim]+[BF4]- was recovered and recycled in our previous work. Please refer to ref. 12.