A. Wagner et al.
SHORT COMMUNICATION
Toledo for providing us a prototype of their Quantos® powder
dosing system.
[8] a) P. Tundo, A. Perosa, Reactive Funct Polym. 2003, 54, 95–
101; b) A. Mori, T. Mizusaki, M. Kawase, T. Maegawa, Y.
Monguchi, S. Takao, Y. Takagi, H. Sajiki, Adv. Synth. Catal.
2008, 350, 406–410; c) A. Mori, T. Mizusaki, Y. Miyakawa, E.
Ohashi, T. Haga, T. Maegawa, Y. Monguchi, H. Sajiki, Tetra-
hedron 2006, 62, 11925–11932.
[9] a) J. Madsen, C. Viuf, M. Bols, Chem. Eur. J. 2000, 6, 1140–
1146; b) K. R. Rawal, S. Rani, N. Kumari, Y. D. Vankar, J.
Org. Chem. 2009, 74, 5349–5355; c) L. Zhou, W. Wang, L. Zuo,
S. Yao, W. Wang, W. Duan, Tetrahedron Lett. 2008, 49, 4876–
4878.
[10] a) M. Akinori, S. Hironao, Gifu Yakka Daigaku Kiyo 2008, 57,
45–53; b) O. Keiji, S. Mutsumi, Yuki Gosei Kagaku Kyokaishi
2007, 65, 379–381.
[11] a) P. N. Rylander in Best Synthetic Methods – Hydrogenation
Methods, Academic Press, Harcourt Brace and Company Pub-
lishers, London, 1985, ch. 1–11; b) R. L. Augustine in Hetero-
geneous Catalysis for Synthetic Chemist, Dekker, New York,
1995; c) M. Frielander in Practical Catalytic Hydrogenation:
Techniques and Applications, Wiley, New York, 1971.
[1]
[2]
N. A. Afagh, A. K. Yudin, Angew. Chem. Int. Ed. 2010, 49,
262–310.
a) M. T. Reetz, Angew. Chem. Int. Ed. 2002, 41, 1335–1338; b)
J. G. De Vries, A. H. M. De Vries, Eur. J. Org. Chem. 2003,
799–811.
[3]
a) S. J. Taylor, J. P. Morken, Science 1998, 280, 267–270; b)
M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holtzwarth, An-
gew. Chem. Int. Ed. 1998, 37, 2647–2650.
[4] a) M. T. Reetz, K. M. Kühling, A. Deege, H. Hinrichs, D.
Belder, Angew. Chem. Int. Ed. 2000, 39, 3891–3893; b) Y.
Zhang, X. Gong, H. Zhang, R. C. Larock, E. S. Yeung, J.
Comb. Chem. 2000, 2, 450–452.
[5] a) M. T. Reetz, M. H. Becker, H. W. Klein, D. A. Stöckigt, An-
gew. Chem. Int. Ed. 1999, 38, 1758–1761; b) J. Guo, J. Wu, G.
Siuzdak, M. G. Finn, Angew. Chem. Int. Ed. 1999, 38, 1755–
1758; c) J. W. Szewczyk, R. L. Zuckerman, R. G. Bergman, [12] M. J. Gaunt, J. Yu, J. B. Spencer, J. Org. Chem. 1998, 63, 4172–
J. A. Ellman, Angew. Chem. Int. Ed. 2001, 40, 219–219; d) C.
Market, A. Pfaltz, Angew. Chem. Int. Ed. 2004, 43, 2498–2500.
[6] P. Vicennati, N. Bensel, A. Wagner, C. Créminion, F. Taran,
Angew. Chem. Int. Ed. 2005, 44, 2–6.
[7] a) F. Badalassi, D. Wahler, G. Klein, P. Crotti, J.-L. Reymond,
Angew. Chem. Int. Ed. 2000, 39, 4067–4070; b) K. H. Shaugh-
nessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121,
2123–2132; c) F. Tanaka, R. Thayumanavan, C. F. Barbas III,
J. Am. Chem. Soc. 2003, 125, 8523–8528.
4173.
[13] An equimolar mixture of substrates 2 and 2a was reacted under
the selected conditions. The results were in line with expecta-
tions according to the analysis in Figure 1. S1–C1, S1–C8 and
S8–C10 gave mostly complete reduction of both substrates. S1–
C4 gave less than 10% reduction and S6–C10 resulted in a mix-
ture of starting materials and reduced compounds.
Received: December 23, 2009
Published Online: March 10, 2010
2264
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Eur. J. Org. Chem. 2010, 2261–2264