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Synlett 2011(8): 1121-1124  
DOI: 10.1055/s-0030-1259937
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Aerobic Oxidation of Cyclic Amines to Lactams Catalyzed by PVP-Stabilized Nanogold

Patcharee Preedasuriyachaia,b, Warinthorn Chavasiric, Hidehiro Sakurai*b,d,e
a Program in Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
b Department of Functional Molecular Science, The Graduate University for Advanced Studies, Myodaiji, Okazaki 444-8787, Japan
c Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
d Research Center for Molecular Scale Nanoscience, Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan
Fax: +81(564)595527; e-Mail: hsakurai@ims.ac.jp;
e PRESTO, Japan Science and Technology Agency, Tokyo 102-0075, Japan
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Publikationsverlauf

Received 15 January 2011
Publikationsdatum:
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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22

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.