Job/Unit: O21595
/KAP1
Date: 20-02-13 12:47:12
Pages: 7
Cobalt(II)–Porphyrin-Catalyzed Aerobic Oxidation
119, 4618–4622; Angew. Chem. Int. Ed. 2007, 46, 4534–4538;
(1.0 mL) were added to a 25 mL flame-dried Schlenk tube in air.
The air was removed by vacuum, and O2 (1 atm) was introduced.
The Schlenk tube was then sealed, and the resulting mixture was
stirred at 60 °C under an atmosphere of oxygen (1 atm). After stir-
ring for the time indicated, the mixture was cooled to room tem-
perature, carefully acidified with dilute aqueous HCl, diluted with
ethyl acetate (10 mL), filtered through a plug of silica gel, and
washed with ethyl acetate (20–30 mL). The combined organic ex-
tract was dried with anhydrous MgSO4, filtered, and concentrated
under reduced pressure. The resulting residue was purified by col-
umn chromatography on silica gel to afford the desired product.
d) L. Palais, I. S. Mikhel, C. Bournaud, L. Micouin, C. A. Fal-
ciola, M. Vuagnoux-d’Augustin, S. Rosset, G. Bernardinelli, A.
Alexakis, Angew. Chem. 2007, 119, 7606–7609; Angew. Chem.
Int. Ed. 2007, 46, 7462–7465; e) J. Wang, X. Hu, J. Jiang, S.
Gou, X. Huang, X. Liu, X. Feng, Angew. Chem. 2007, 119,
8620–8622; Angew. Chem. Int. Ed. 2007, 46, 8468–8470; f) Z.
Hua, V. C. Vassar, H. Choi, I. Ojima, Proc. Natl. Acad. Sci.
USA 2004, 101, 5411–5416; g) A. Alexakis, C. Benhaim, S.
Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262–5263.
[7]
a) J. Doussot, A. Guy, C. Ferroud, Tetrahedron Lett. 2000, 41,
2545–2547; b) K. Ding, Y. Wang, L. Zhang, Y. Wu, Tetrahe-
dron 1996, 52, 1005–1010; c) H. Ishino, N. Itoh, M. Nagash-
ima, K. Kurosawa, Bull. Chem. Soc. Jpn. 1992, 65, 620–622; d)
M. Hovorka, J. Günterová, J. Závada, Tetrahedron Lett. 1990,
31, 413–416; e) F. Toda, K. Tanaka, S. Iwata, J. Org. Chem.
1989, 54, 3007–3009; f) K. Yamamoto, H. Fukushima, Y. Oka-
moto, K. Hatada, M. Nakazaki, J. Chem. Soc., Chem. Com-
mun. 1984, 1111–1112; g) B. Feringa, H. Wynberg, J. Org.
Chem. 1981, 46, 2547–2557; h) B. Feringa, H. Wynberg, Tetra-
hedron Lett. 1977, 18, 4447–4450; i) M. J. S. Dewar, T. Nakaya,
J. Am. Chem. Soc. 1968, 90, 7134–7135.
Supporting Information (see footnote on the first page of this arti-
cle): Experiment details, characterization data, and copies of the
NMR spectra of products 2a–2l.
Acknowledgments
This project was financially supported by the Chinese National
Natural Science Fund.
[8]
For selected reports on enantioselective oxidative biaryl cou-
pling, see: a) H. Egami, K. Matsumoto, T. Oguma, T. Kunisu,
T. Katsuki, J. Am. Chem. Soc. 2010, 132, 13633–13635; b) H.
Egami, T. Katsuki, J. Am. Chem. Soc. 2009, 131, 6082–6083;
c) S. Takizawa, Chem. Pharm. Bull. 2009, 57, 1179–1188; d) S.
Takizawa, T. Katayama, C. Kameyama, K. Onitsuka, T. Su-
zuki, T. Yanagida, T. Kawai, H. Sasai, Chem. Commun. 2008,
1810–1812; e) Q.-X. Guo, Z.-J. Wu, Z.-B. Luo, Q.-Z. Liu, J.-L.
Ye, S.-W. Luo, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 2007,
129, 13927–13938; f) M. Tada, N. Kojima, Y. Izumi, T. Taniike,
Y. Iwasawa, J. Phys. Chem. B 2005, 109, 9905–9916; g) M.
Tada, T. Taniike, L. M. Kantam, Y. Iwasawa, Chem. Commun.
2004, 2542–2543; h) H. Somei, Y. Asano, T. Yoshida, S. Takiz-
awa, H. Yamataka, H. Sasai, Tetrahedron Lett. 2004, 45, 1841–
1844; i) J. Gao, J. H. Reibenspies, A. E. Martell, Angew. Chem.
2003, 115, 6190–6194; Angew. Chem. Int. Ed. 2003, 42, 6008–
6012; j) X. Li, J. B. Hewglay, C. A. Mulrooney, J. Yang, M. C.
Kozlowski, J. Org. Chem. 2003, 68, 5500–5511; k) Z. Luo, Q.
Liu, L. Gong, X. Cui, A. Mi, Y. Jiang, Angew. Chem. 2002,
114, 4714–4717; Angew. Chem. Int. Ed. 2002, 41, 4532–4535; l)
N. B. Barhate, C.-T. Chen, Org. Lett. 2002, 4, 2529–2532; m)
S.-W. Hon, C.-H. Li, J.-H. Kuo, N.-B. Barhate, Y.-H. Liu, Y.
Wang, C.-T. Chen, Org. Lett. 2001, 3, 869–872; n) X. Li, J.
Yang, M. C. Kozlowski, Org. Lett. 2001, 3, 1137–1140.
[1] a) A. de Meijere, F. Diederich (Eds.), Metal-Catalyzed Cross-
Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, Germany,
2004, vol. 1 and 2; b) F. Diederich, P. J. Stang (Eds.), Metal-
Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim,
Germany, 1998.
[2] a) L. Ackermann, Chem. Rev. 2011, 111, 1315–1345; b) C. S.
Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215–1292; c) J.
Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev.
2011, 40, 4740–4761; d) T. Newhouse, P. S. Baran, Angew.
Chem. 2011, 123, 3422–3435; Angew. Chem. Int. Ed. 2011, 50,
3362–3374; e) C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011,
111, 1293–1314; f) L. McMurray, F. O’Hara, M. J. Gaunt,
Chem. Soc. Rev. 2011, 40, 1885–1898; g) W. R. Gutekunst, P. S.
Baran, Chem. Soc. Rev. 2011, 40, 1976–1991; h) T. W. Lyons,
M. S. Sanford, Chem. Rev. 2010, 110, 1147–1169; i) L.-M. Xu,
Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712–733; j) C.-L.
Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677–685; k)
O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009,
42, 1074–1086; l) L. Ackermann, R. Vicente, A. R. Kapdi, An-
gew. Chem. 2009, 121, 9976–10011; Angew. Chem. Int. Ed.
2009, 48, 9792–9826; m) W. Wu, W. Su, J. Am. Chem. Soc.
2011, 133, 11924–11927; n) W. Wu, J. Xu, S. Huang, W. Su,
Chem. Commun. 2011, 47, 9660–9662.
[3] a) A. E. Wendlandt, A. M. Suess, S. S. Stahl, Angew. Chem.
2011, 123, 11256–11283; Angew. Chem. Int. Ed. 2011, 50,
11062–11087; b) J. A. Ashenhurst, Chem. Soc. Rev. 2010, 39,
540–548; c) H. Wang, Chirality 2010, 22, 827–837; d) M. C.
Kozlowski, B. J. Morgan, E. C. Linton, Chem. Soc. Rev. 2009,
38, 3193–3207; e) J. M. Brunel, Chem. Rev. 2005, 105, 857–898.
[4] a) S. K. Quideau, S. Feldman, Chem. Rev. 1996, 96, 475–504;
b) D. J. Tweardy, X. Huang, M. M. Kasembeli, Patent WO
149192 A1, 2009; c) G. Bringmann, C. Günther, M. Ochse, O.
Schupp, S. Tasler, in: Progress in the Chemistry of Organic Nat-
ural Products (Eds.: W. Herz, H. Falk, G. W. Kirby, R. E.
Moore), Springer, Vienna, 2001, vol. 82, pp. 1–249.
[5] a) A. N. Carnrnidge, R. J. Bushby, in: Handbook of Liquid
Crystals (Eds.: D. Demus, J. W. Goodby, G. W. Gray, H.-W.
Spiess, V. Vill), Wiley-VCH, Weinheim, Germany, 1998, vol.
2B, pp. 693–748; b) K. J. Toyne in Handbook of Liquid Crystals
(Eds.: D. Demus, J. W. Goodby, G. W. Gray, H.-W. Spiess, V.
Vill), Wiley-VCH, Weinheim, Germany, 1998, vol. 2B, pp. 47–
59; c) L. Pu, Chem. Rev. 1998, 98, 2405–2494.
[6] a) J. Wang, W. Wang, W. Li, X. Hu, K. Shen, C. Tan, X. Liu,
X. Feng, Chem. Eur. J. 2009, 15, 11642–11659; b) C. Hawner,
K. Li, V. Cirriez, A. Alexakis, Angew. Chem. 2008, 120, 8334–
8337; Angew. Chem. Int. Ed. 2008, 47, 8211–8214; c) A. G.
Cortez, R. R. Schrock, A. H. Hoveyda, Angew. Chem. 2007,
[9]
For selected reports on homogeneous catalytic aerobic oxidat-
ive biaryl coupling, see: a) B.-S. Liao, Y.-H. Liu, S.-M. Peng,
S.-T. Liu, Dalton Trans. 2012, 41, 1158–1164; b) P. Yan, Y. Su-
giyama, Y. Takahashi, H. Kinemuchi, T. Temma, S. Habaue,
Tetrahedron 2008, 64, 4325–4331; c) S. Habaue, T. Temma, Y.
Sugiyama, P. Yan, Tetrahedron Lett. 2007, 48, 8595–8598; d)
J. K. Joseph, S. L. Jain, B. Sain, Catal. Commun. 2006, 7, 184–
186; e) S.-Y. Zhang, J.-B. Lan, X.-Y. Su, S.-J. Guo, L. Chen, J.-
S. You, R.-G. Xie, J. Chem. Res. 2005, 7, 418–419; f) P. S. Um-
are, G. L. Tembe, React. Kinet. Catal. Lett. 2004, 82, 173–178;
g) V. B. Sharma, S. L. Jain, B. Sain, Tetrahedron Lett. 2003, 44,
2655–2656; h) J. S. Yadav, B. V. S. Reddy, K. U. Gayathri, A. R.
Prasad, New J. Chem. 2003, 27, 1684–2686; i) R. Gupta, R.
Mukherjee, Tetrahedron Lett. 2000, 41, 7763–7767; j) D.-R.
Hwang, C.-P. Chen, B.-J. Uang, Chem. Commun. 1999, 1207–
1208; k) H. Nishino, H. Satoh, M. Yamashita, K. Kurosawa,
J. Chem. Soc. Perkin Trans. 2 1999, 1919–1924.
For selected reports on heterogeneous catalytic aerobic oxidat-
ive biaryl coupling, see: a) H. Eshghi, M. Bakavoli, H. Moradi,
Chin. Chem. Lett. 2009, 20, 663–667; b) M. Matsushita, K.
Kamata, K. Yamaguchi, N. Mizuno, J. Am. Chem. Soc. 2005,
127, 6632–6640; c) T. Ikeda, N. Misawa, Y. Ichihashi, S. Nishi-
yama, S. Tsuruya, J. Mol. Catal. A 2005, 231, 235–240; d) K.
Iwai, T. Yamauchi, K. Hashimoto, T. Mizugaki, K. Ebitani,
[10]
Eur. J. Org. Chem. 0000, 0–0
© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
5