Palladium-Catalyzed One-Pot Conversion of Aldehydes to Amides
Scheme 3. Proposed catalytic cycle.
Table 3. Pd-catalyzed conversion of alkyl and allyl aldehydes
to amides.
References
[1] a) R. C. Larock, in Comprehensive Organic Transfor-
mations: A Guide to Functional Group Preparations,
2nd edn., John Wiley & Sons, Inc., New York, USA,
1999; b) Comprehensive Organometallic Chemistry II,
(Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Perga-
mon, Oxford, 1995; c) B. Cornils, W. A. Hermann, in
Applied Homogeneous Catalysis with Organometallic
Compounds, VCH, New York, 1996; d) Transition
Metals for Organic Synthesis, (Eds.: M. Beller, C.
Bolm), Wiley-VCH, Weinheim, 1998.
[2] a) C. E. Mabermann, in: Encyclopedia of Chemical
Technology, Vol. 1, (Ed: J. I. Kroschwitz), Wiley, New
York, 1991, pp 251–266; b) D. Lipp, in: Encyclopedia
of Chemical Technology, Vol., 1 (Ed.: J. I. Kroschwitz),
Wiley, New York, 1991, pp 266–287; c) R. Opsahl, in:
Encyclopedia of Chemical Technology, Vol. 2, (Ed: J. I.
Kroschwitz), Wiley, New York, 1991, pp. 346–356.
[3] a) H. Sharghi, M. H. Saravari, J. Chem. Res. Miniprint
2001, 446–449; b) H. Sharghi, M. H. Sarvari, Tetrahe-
dron 2002, 58, 10323–10328; c) H. Sharghi, M. Hossei-
ni, Synthesis 2002, 1057–1060.
[a]
To
H2NOH·HCl (0.6 mmol) and Cs2CO3 (0.6 mmol) in
DMSO:H2O (3:1, 2 mL) at 1008C for 5–7 h, Pd(OAc)2
(5 mol%) was added and the reaction mixture was stirred
for the additional 9–10 h.
a
stirred solution of aldehyde (0.5 mmol),
AHCTUNGTRENNUNG
[4] H. Fujiwara, Y. Ogasawara, K. Yamaguchi, N. Mizuno,
Angew. Chem. 2007, 119, 5294–5297; Angew. Chem.
Int. Ed. 2007, 46, 5202–5205.
[b]
Isolated yield.
[5] N. A. Owston, A. J. Parker, J. M. J. Willims, Org. Lett.
2007, 9, 73–75.
[6] D. Gnanamgari, R. H. Crabtree, Organometallics 2009,
28, 922–924.
[7] a) R. A. Sheldon, Pure Appl. Chem. 2000, 72, 1233–
1246; b) T. Punniyamurthy, L. Rout, Coord. Chem. Rev.
2008, 252, 134–154.
Supporting Information
Characterization data and NMR (1H and 13C) spectra of all
the amides are given in the Supporting Information.
[8] Aqueous organic reactions have attracted considerable
attention. For some examples, see: a) C.-J. Li, T.-H.
Chan, in: Organic Reactions in Aqueous Media, Wiley,
New York, 1997; b) P. T. Anastas, J. C. Warner, in:
Green Chemistry: Theory and Practice, Oxford Univer-
sity Press, London, 1998; c) P. A. Grieco, in: Organic
Synthesis in Water, Blackie Academic and Professional,
Acknowledgements
We thank Department of Science and Technology, New
Delhi, and Council of Scientific and Industrial Research,
New Delhi, for financial support.
Adv. Synth. Catal. 2010, 352, 288 – 292
ꢀ 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
291