7
(a) S. Rau, D. Walthera and J. G. Vosb, Dalton Trans., 2007, 915–919;
b) M. A. Ischay, M. E. Anzovino, J. Du and T. P. Yoon, J. Am. Chem.
Soc., 2008, 130(39), 12886–12887; (c) H. Schmaderer, P. Hilgers, R.
Lechner and B. K o¨ nig, Adv. Synth. Catal., 2009, 351, 163–174; (d) G.
Imperato and B. K o¨ nig, ChemSusChem, 2008, 1, 993–996; (e) J.
Svoboda, H. Schmaderer and B. K o¨ nig, Chem.–Eur. J., 2008, 14,
19 For typical chemical methods of reduction, see: (a) Y. Zheng, K. Ma,
H. Wang, X. Sun, J. Jiang, C. Wang, R. Li and J. Ma, Catal. Lett.,
2008, 124, 268–276; (b) M. O. Sydnes and M. Isobe, Tetrahedron
Lett., 2008, 49, 1199–1202; (c) H. H. Hodgson and E. R. Ward,
J. Chem,. Soc., 1949, 1316; (d) D. S. Wulfman and C. F. Cooper,
Synthesis, 1978, 924–925.
(
1
2
2
854–1865; (f) R. Cibulka, R. Vasold and B. K o¨ nig, Chem.–Eur. J.,
004, 10, 6223–6231; (g) J. Du and T. P. Yoon, J. Am. Chem. Soc.,
009, 131, 14604.
S. Rau, B. Sch a¨ fer, D. Gleich, E. Anders, M. Rudolph, M. Friedrich,
H. G o¨ rls, W. Henry and J. G. Vos, Angew. Chem., 2006, 118, 6361–
364.
20 (a) H. Tada, A. Takao, T. Akita and K. Tanaka, ChemPhysChem,
2006, 7, 1687–1691; (b) Y. Matsushita, S. Kumada, K. Wakabayashi,
K. Sakeda and T. Ichimura, Chem. Lett., 2006, 35(4), 410–411; (c) H.
Tada, T. Ishida, A. Takao, S. Ito, S. Mukhopadhay, T. Akita, K.
Tanaka and H. Kobayashi, ChemPhysChem, 2005, 6, 1537–1543;
(d) J. L. Ferry and W. H. Glaze, J. Phys. Chem. B, 1998, 102,
8
9
6
ˇ
D. A. Nicewicz and D. W. C. MacMillan, Science, 2008, 322, 77–80.
2239–2244; (e) V. Brezov a´ , A. Bla zˇ kov a´ , I. Surina and B. Havlinov a´ ,
1
0 (a) A. Bauer, F. Westk a¨ mpfer, S. Grimme and T. Bach, Nature, 2005,
J. Photochem. Photobiol., A, 1997, 107, 233–237.
21 H. Tada, T. Ishida, A. Takao and S. Ito, Langmuir, 2004, 20, 7898–
7900.
4
5
36, 1139–1140; (b) J. Svoboda and B. K o¨ nig, Chem. Rev., 2006, 106,
413–5430.
1
1
1 M. Fagnoni, D. Dond, D. Ravelli and A. Albini, Chem. Rev., 2007,
22 S. O. Flores, O. Rios-Bernij, M. A. Valenzuela, I. Cordova, R. Gomez
and R. Guti e´ rrez, Top. Catal., 2007, 44(4), 507–511.
23 Recent review: J.-H. Yum, P. Chen, M. Graetzel and M. K.
Nazeeruddin, ChemSusChem, 2008, 1, 699–707.
24 S. Chen and K. Kimura, J. Phys. Chem. B, 2001, 105, 5397–
5403.
25 E. Kolwaska, H. Remita, C. Colbeau-Justin, J. Hupka and J. Belloni,
J. Phys. Chem. C, 2008, 112(4), 1124–1131.
26 J. I. L. Chen, E. Loso, N. Ebrahim and G. A. Ozin, J. Am. Chem.
Soc., 2008, 130, 5420–5421.
27 The use of TEOA for the photoreduction is essential. A replacement
1
07, 2725–2756.
2 (a) S. In, A. Orlov, R. Berg, F. Garc ´ı a, S. Pedrosa-Jimenez, M. S.
Tikhov, D. S. Wright and R. M. Lambert, J. Am. Chem. Soc., 2007,
1
29, 13790–13791; (b) R. Nakamura, A. Okamoto, H. Osawa, H.
Irie and K. Hashimoto, J. Am. Chem. Soc., 2007, 129, 9596–9597;
c) S. S. Srinivasan, J. Wade and E. K. Stefanakos, J. Nanomat., 2006,
–4.
(
1
1
3 (a) W. R. Duncan, C. F. Craig and O. V. Prezhdo, J. Am. Chem.
Soc., 2007, 129, 8528–8543; (b) H. Qin, S. Wenger, M. Xu, F. Gao,
X. Jing, P. Wang, S. M. Zakeeruddin and M. Gr a¨ tzel, J. Am. Chem.
Soc., 2008, 130, 9202–9203; (c) F. Gao, Y. Wang, D. Shi, J. Zhang,
M. Wang, X. Jing, R. Humphry-Baker, P. Wang, S. M. Zakeeruddin
and M. Gr a¨ tzel, J. Am. Chem. Soc., 2008, 130, 10720–10728.
3
by NEt as the terminal reductant leads to a drastically decreased
activity, which indicates the importance of the presence of protons
for the overall photoreduction.
1
1
4 H. C. Pehlivanugullari, E. Sumer and H. Kisch, Res. Chem. Intermed.,
28 The chemoselective hydrogenation of substituted nitrobenzenes
depending on the nature of the catalytically active metal and the
catalyst support was described recently: A. Corma, P. Serna, P.
Concepci o´ n and J. J. Calvino, J. Am. Chem. Soc., 2008, 130, 8748–
8753.
2
007, 33, 297–309.
5 (a) H. Takeda, K. Koike, H. Inoue and O. Ishitani, J. Am. Chem. Soc.,
2
008, 130, 2023–2031; (b) W. R. McNamara, R. C. Snoeberger, G.
Li, J. M. Schleicher, C. W. Cady, M. Poyatos, C. A. Schmuttenmaer,
R. H. Crabtree, G. W. Brudvig and V. S. Batista, J. Am. Chem. Soc.,
29 B. H. Kim, Y. Jin, Y. M. Jun, R. Han, W. Baik and B. M. Lee,
Tetrahedron Lett., 2000, 41, 2137–2140.
2
008, 130, 14329–14338; (c) P. Du, J. Schneider, F. Li, W. Zhao, U.
Patel, F. N. Castellano and R. Eisenberg, J. Am. Chem. Soc., 2008,
30, 5056–5058.
6 O. Ozcan, F. Yukruk, E. U. Akkaya and D. Uner, Top. Catal., 2007,
4(4), 523–528.
30 P. G. Hoertz, A. Staniszewski, A. Marton, G. T. Higgins, C. D.
Incarvito, A. L. Rheingold and G. J. Meyer, J. Am. Chem. Soc.,
2006, 128, 8234–8245.
31 M. K. Nazeeruddin, A. Kay, I. Rodicio, R. Humphry-Baker, E.
M u¨ ller, P. Lisa, N. Vlachopoulos and M. Gr a¨ tzel et al., J. Am. Chem.
Soc., 1993, 115, 6382–6390.
1
1
1
1
4
7 G. Li, N. M. Dimitrijevic, L. Chen, J. M. Nichols, T. Rajh and K. A.
Gray, J. Am. Chem. Soc., 2008, 130, 5402–5403.
8 M. Zhang, C. Chen, W. Ma and J. Zhao, Angew. Chem., 2008, 120,
32 P. Swoboda, R. Saf and K. Hummel, Macromolecules, 1995, 28,
4255–4259.
9
876–9879.
4
06 | Green Chem., 2010, 12, 400–406
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