1124
P. Preedasuriyachai et al.
LETTER
(5) (a) Tamaru, Y.; Yamada, Y.; Yoshida, Z. Synthesis 1983,
474. (b) Noata, T.; Murahashi, S.-i. Synlett 1991, 693.
(c) Tillack, A.; Rudloff, I.; Beller, M. Eur. J. Org. Chem.
2001, 523. (d) 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, J. Y.; 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.
(16) (a) Tsunoyama, H.; Sakurai, H.; Ichikuni, N.; Negishi, Y.;
Tsukuda, T. Langmuir 2004, 20, 11293. (b) Sakurai, H.;
Tsunoyama, H.; Tsukuda, T. J. Organomet. Chem. 2007,
692, 368.
(17) (a) Tsunoyama, H.; Sakurai, H.; Negishi, Y.; Tsukuda, T.
J. Am. Chem. Soc. 2005, 127, 9374. (b) Tsunoyama, H.;
Sakurai, H.; Tsukuda, T. Chem. Phys. Lett. 2006, 429, 528.
(c) Tsunoyama, H.; Tsukuda, T.; Sakurai, H. Chem. Lett.
2007, 36, 212. (d) Chaki, N. K.; Tsunoyama, H.; Negishi,
Y.; Sakurai, H.; Tsukuda, T. J. Phys. Chem. C 2007, 111,
4885. (e) Kanaoka, S.; Yagi, N.; Fukuyama, Y.; Aoshima,
S.; Tsunoyama, H.; Tsukuda, T.; Sakurai, H. J. Am. Chem.
Soc. 2007, 129, 12060. (f) 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.
(19) (a) Kamiya, I.; Tsunoyama, H.; Tsukuda, T.; Sakurai, H.
Chem. Lett. 2007, 36, 646. (b) Kitahara, H.; Kamiya, I.;
Sakurai, H. Chem. Lett. 2009, 38, 908. (c) Kitahara, H.;
Sakurai, H. Chem. Lett. 2010, 39, 46.
(15) (a) Zhu, B.; Angelici, R. J. Chem. Commun. 2007, 2157.
(b) Angelici, R. J. J. Organomet. Chem. 2008, 693, 847.
(c) Zhu, B.; Lazar, M.; Trewyn, B. G.; Angelici, R. J.
J. Catal. 2008, 260, 1. (d) Grirrane, A.; Corma, A.; Garcia,
H. Science 2008, 322, 1661. (e) So, M.-H.; Liu, Y.; Ho,
C.-M.; Che, C.-M. Chem. Asian J. 2009, 4, 1551.
(f) Aschwanden, L.; Mallat, T.; Krumeich, F.; Baiker, A.
J. Mol. Catal. A: Chem. 2009, 309, 57. (g) Grirrane, A.;
Corma, A.; Garcia, H. J. Catal. 2009, 264, 138.
(h) Aschwanden, L.; Panella, B.; Rossbach, P.; Keller, B.;
Baiker, A. ChemCatChem 2009, 1, 111. (i) Aschwanden,
L.; Mallat, T.; Maciejewski, M.; Krumeich, F.; Baiker, A.
ChemCatChem 2010, 2, 666. (j) Zhou, Y.; Angelici, R. J.;
Woo, L. K. Catal. Lett. 2010, 137, 8.
(20) Preedasuriyachai, P.; Kitahara, H.; Sakurai, H. Chem. Lett.
2010, 39, 1174.
(21) Zhou, W.; Zhang, L.; Jiao, N. Tetrahedron 2009, 65, 1982.
(22) Typical Procedure for the Oxidation of 1a Catalyzed by
Au:PVP under NaOH/H2O–EtOH Conditions
A test tube (f = 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.
Synlett 2011, No. 8, 1121–1124 © Thieme Stuttgart · New York