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DOI: 10.1055/s-0030-1259937
Aerobic Oxidation of Cyclic Amines to Lactams Catalyzed by PVP-Stabilized Nanogold
Publication History
Publication Date:
07 April 2011 (online)
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Abstract
Gold nanoclusters stabilized by poly(N-vinyl-2-pyrrolidone) (Au:PVP) are active and selective catalysts under aerobic conditions for oxidation of cyclic secondary amines at the α-position of the nitrogen atom. The catalyst accelerates the formation of the imines by oxidation of the amines in aqueous solvent to afford the corresponding lactams.
Key words
gold nanoclusters - amine - oxidation - amide
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1a
Bäckvall J.-E. In Modern Oxidation MethodsBäckvall J.-E. Wiley-VCH; Weinheim: 2004. p.193 -
1b
Murahashi S.-I.Komiya N. In Ruthenium in Organic SynthesisMurahashi S.-I. Wiley-VCH; Weinheim: 2004. p.53 -
1c
Pina CD.Falletta E.Rossi M. Top. Catal. 2007, 44: 325 -
2a
Ochiai M.Kajishima D.Sueda T. Tetrahedron Lett. 1999, 40: 5541 -
2b
Huang W.-J.Singh OV.Chen C.-H.Chiou S.-Y.Lee S.-S. Helv. Chim. Acta 2002, 85: 1069 -
2c
Sueda T.Kajishima D.Goto S. J. Org. Chem. 2002, 68: 3307 - 3
Venkov AP.Statkova-Abeghe SM. Tetrahedron 1996, 52: 1451 - 4
Mohamed MA.Yamada K.-I.Tomioka K. Tetrahedron Lett. 2009, 50: 3436 -
5a
Tamaru Y.Yamada Y.Yoshida Z. Synthesis 1983, 474 -
5b
Noata T.Murahashi S.-i. Synlett 1991, 693 -
5c
Tillack A.Rudloff I.Beller M. Eur. J. Org. Chem. 2001, 523 -
5d
Yoo W.-J.Li C.-J. J. Am. Chem. Soc. 2006, 128: 13064 - 6
Nakagawa K.Onoue H.Minami K. Chem. Commun. 1996, 17 - 7
An G.-i.Kim M.Kim JY.Rhee H. Tetrahedron Lett. 2003, 44: 2183 - 8
Ekoue-Kovi K.Wolf C. Org. Lett. 2007, 9: 3429 - 9
Gao J.Wang G.-W. J. Org. Chem. 2008, 73: 2955 - 10
Punniyamurthy T.Velusamy S.Iqbal J. Chem. Rev. 2005, 105: 2329 - 11
Mizuno N.Yamaguchi K. Catal. Today 2008, 132: 18 - 12
Kodama S.Yoshida J.Nomoto A.Ueta Y.Yano S.Ueshima M.Ogawa A. Tetrahedron Lett. 2010, 51: 2450 - 13
Maeda Y.Nishimura T.Uemura S. Bull. Chem. Soc. Jpn. 2003, 76: 2399 - 14
Wang J.-R.Fu Y.Zhang B.-B.Cui X.Liu L.Guo Q.-X. Tetrahedron Lett. 2006, 47: 8293 -
15a
Zhu B.Angelici RJ. Chem. Commun. 2007, 2157 -
15b
Angelici RJ. J. Organomet. Chem. 2008, 693: 847 -
15c
Zhu B.Lazar M.Trewyn BG.Angelici RJ.
J. Catal. 2008, 260: 1 -
15d
Grirrane A.Corma A.Garcia H. Science 2008, 322: 1661 -
15e
So M.-H.Liu Y.Ho C.-M.Che C.-M. Chem. Asian J. 2009, 4: 1551 -
15f
Aschwanden L.Mallat T.Krumeich F.Baiker A. J. Mol. Catal. A: Chem. 2009, 309: 57 -
15g
Grirrane A.Corma A.Garcia H. J. Catal. 2009, 264: 138 -
15h
Aschwanden L.Panella B.Rossbach P.Keller B.Baiker A. ChemCatChem 2009, 1: 111 -
15i
Aschwanden L.Mallat T.Maciejewski M.Krumeich F.Baiker A. ChemCatChem 2010, 2: 666 -
15j
Zhou Y.Angelici RJ.Woo LK. Catal. Lett. 2010, 137: 8 -
16a
Tsunoyama H.Sakurai H.Ichikuni N.Negishi Y.Tsukuda T. Langmuir 2004, 20: 11293 -
16b
Sakurai H.Tsunoyama H.Tsukuda T. J. Organomet. Chem. 2007, 692: 368 -
17a
Tsunoyama H.Sakurai H.Negishi Y.Tsukuda T.
J. Am. Chem. Soc. 2005, 127: 9374 -
17b
Tsunoyama H.Sakurai H.Tsukuda T. Chem. Phys. Lett. 2006, 429: 528 -
17c
Tsunoyama H.Tsukuda T.Sakurai H. Chem. Lett. 2007, 36: 212 -
17d
Chaki NK.Tsunoyama H.Negishi Y.Sakurai H.Tsukuda T. J. Phys. Chem. C 2007, 111: 4885 -
17e
Kanaoka S.Yagi N.Fukuyama Y.Aoshima S.Tsunoyama H.Tsukuda T.Sakurai H. J. Am. Chem. Soc. 2007, 129: 12060 -
17f
Tsunoyama H.Ichikuni N.Sakurai H.Tsukuda T. J. Am. Chem. Soc. 2009, 127: 7086 - 18
Sakurai H.Tsunoyama H.Tsukuda T. Trans. Mater. Res. Soc. Jpn. 2006, 31 521: 8 -
19a
Kamiya I.Tsunoyama H.Tsukuda T.Sakurai H. Chem. Lett. 2007, 36: 646 -
19b
Kitahara H.Kamiya I.Sakurai H. Chem. Lett. 2009, 38: 908 -
19c
Kitahara H.Sakurai H. Chem. Lett. 2010, 39: 46 - 20
Preedasuriyachai P.Kitahara H.Sakurai H. Chem. Lett. 2010, 39: 1174 - 21
Zhou W.Zhang L.Jiao N. Tetrahedron 2009, 65: 1982
References and Notes
Typical Procedure
for the Oxidation of 1a Catalyzed by Au:PVP under NaOH/H
2
O-EtOH
Conditions
A test tube (ϕ = 30
mm) was placed with 1a (13.3 mg, 0.10 mmol),
NaOH (8 mg, 0.20 mmol), and EtOH (5 mL). The aq solution of Au:PVP
(1 mM, 10 mL = 10 atom%) was
added, and the reaction mixture was stirred vigorously (1300 rpm) at
27 ˚C or 50 ˚C for 24 h. The reaction mixture
was extracted with EtOAc (3 × 10 mL),
and then washed the organic layers with brine, dried over Na2SO4,
and concen-trated in vacuo. The crude products were separated by preparative
TLC.