S. Enthaler et al. / Tetrahedron Letters 53 (2012) 882–885
885
Scheme 1. Mechanistical investigations.
348, 1029–1032; (k) Bandini, M.; Melucci, M.; Piccinelli, F.; Sinisi, R.; Tommasi,
S.; Umani-Ronchi, A. Chem. Commun. 2007, 4519–4521; (l) Inagaki, T.; Yamada,
Y.; Phong, L. T.; Furuta, A.; Ito, J.-i.; Nishiyama, H. Synlett 2009, 253–256; (m)
Gajewy, J.; Kwit, M.; Gawron´ ski, J. Adv. Synth. Catal. 2009, 351, 1055–1063; (n)
Das, S.; Addis, D.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2010, 132,
1770–1771.
as starting materials. Excellent yields and selectivities were feasible
under optimized conditions.
Acknowledgments
5. (a) Marinos, N. A.; Enthaler, S.; Driess, M. ChemCatChem 2010, 2, 846–853; (b)
Enthaler, S.; Eckhardt, B.; Inoue, S.; Irran, E.; Driess, M. Chem. Asian J. 2010, 5,
2027–2035; (c) Enthaler, S.; Schröder, K.; Inoue, S.; Eckhardt, B.; Junge, K.;
Beller, M.; Driess, M. Eur. J. Org. Chem. 2010, 4893–4901; (d) Enthaler, S. Catal.
Lett. 2011, 141, 55–61; (e) Enthaler, S. Catal. Sci. Technol. 2011, 1, 104–110.
7. Larock, R. C. Comprehensive Organic Transformations, Wiley, 2010.
8. A selection for metal-catalyzed transformations of aldoximes: (a) Yang, S. H.;
Sukbok, C. Org. Lett. 2001, 3, 4209–4211; (b) Kim, H. S.; Kim, S. H.; Kim, J. N.
Tetrahedron Lett. 2009, 50, 1717–1719; (c) Kim, E. S.; Kim, H. S.; Kim, J. N.
Tetrahedron Lett. 2009, 50, 2973–2975; (d) Yadav, L. D. S.; Srivastava, V. P.;
Patel, R. Tetrahedron Lett. 2009, 50, 5532–5535.
Financial support from the Cluster of Excellence ‘Unifying Con-
cepts in Catalysis’ (funded by the Deutsche Forschungsgemeins-
chaft and administered by the Technische Universität Berlin) is
gratefully acknowledged. Furthermore, S. Hennig and D. Bombei
(Technische Universität Berlin) are thanked for technical support.
The authors thank Dr. K. Junge and Bianca Wendt (Leibniz Institut
für Katalyse e.V. an der Universität Rostock) for their support.
References and notes
9. Allen, C. L.; Burel, C.; Williams, J. M. J. Tetrahedron Lett. 2010, 51, 2724–2726.
10. Sharghi, H.; Hosseini, M. Synthesis 2002, 1057–1060.
1. (a) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis; Wiley-VCH:
Weinheim, 2004; (b) Cornils, B.; Herrmann, W. A.; Horváth, I. T.; Leitner, W.;
Mecking, S.; Olivier-Bourbigou, H.; Vogt, D. Multiphase Homogeneous Catalysis;
Wiley-VCH: Weinheim, 2005.
2. (a) Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686–694; (b)
Anastas, P. T.; Kirchhoff, M. M.; Williamson, T. C. Appl. Catal. A 2001, 221, 3–13;
(c) Tucker, J. L. Org. Process Res. Dev. 2010, 14, 328–331; (d) Tucker, J. L. Org.
Process Res. Dev. 2006, 10, 315–319.
11. General procedure for the synthesis of nitriles: A pressure tube was charged
with an appropriate amount of Zn(OTf)2 (0.036 mmol, 5.0 mol %), the
corresponding aldehyde (0.72 mmol) and hydroxylamine hydrochloride
(1.2 equiv, 0.86 mmol). After the addition of toluene (2.0 mL) the reaction
mixture was stirred in a preheated oil bath at 100 °C for 24 h. The mixture was
cooled in an ice bath and biphenyl (internal standard) was added. The solution
was diluted with dichloromethane and an aliquot was taken for GC-analysis
(30 m Rxi-5 ms column, 40–300 °C). The solvent was carefully removed and
the residue was purified by column chromatography (n-hexane/ethyl acetate).
The analytical properties of the corresponding nitriles are in agreement with
the literature.
12. (a) Hatsuda, M.; Seki, M. Tetrahedron 2005, 61, 9908–9917; (b) Zhang, J.; Wang,
Z.; Wang, Y.; Wan, C.; Zheng, X.; Wang, Z. Green Chem. 2009, 11, 1973–1978; (c)
Ramon, R. S.; Marion, N.; Nolan, S. P. Chem. Eur. J. 2009, 15, 8695–8697; (d)
Fergus, S.; Eustace, S. J.; Hegarty, A. F. J. Org. Chem. 2004, 69, 4663–4669; (e)
Ranu, B. C.; Jana, R. J. Org. Chem. 2005, 70, 8621–8624; (f) Panda, K.; Venkatesh,
C.; Ila, H.; Junjappa, H. Eur. J. Org. Chem. 2005, 2045–2055; (g) Ren, Y.; Wang,
W.; Zhao, S.; Tian, X.; Wang, J.; Yin, W.; Cheng, L. Tetrahedron Lett. 2009, 50,
4595–4597; (h) Ebisawa, M.; Ueno, M.; Oshima, Y.; Kondo, Y. Tetrahedron Lett.
2007, 48, 8918–8921.
3. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem. 2008, 120, 3363–3367. Angew
Chem. Int. Ed. 2008, 47, 3317–3321.
4. See a selection for zinc-catalyzed reactions: (a) Mimoun, H.; De Saint Laumer, J.
Y.; Giannini, L.; Scopelliti, R.; Floriani, C. J. Am. Chem. Soc. 1999, 121, 6158–
6166; (b) Mimoun, H. J. Org. Chem. 1999, 64, 2582–2589; (c) Bette, V.;
Mortreux, A.; Lehmann, C. W.; Carpentier, J.-F. Chem. Commun. 2003, 332–333;
(d) Bette, V.; Mortreux, A.; Ferioli, F.; Martelli, G.; Savoia, D.; Carpentier, J.-F.
Eur. J. Org. Chem. 2004, 3040–3045; (e) Bette, V.; Mortreux, A.; Savoia, D.;
Carpentier, J.-F. Tetrahedron 2004, 60, 2837–2842; (f) Mastranzo, V. M.;
Quinterno, L.; Anaya de Parrodi, C.; Juaristi, E.; Walsh, P. J. Tetrahedron 2004,
60, 1781–1789; (g) Ushio, H.; Mikami, K. Tetrahedron Lett. 2005, 46, 2903–
2906; (h) Bette, V.; Mortreux, A.; Savoia, D.; Carpentier, J.-F. Adv. Synth. Catal.
2005, 347, 289–302; (i) Gérard, S.; Pressel, Y.; Riant, O. Tetrahedron: Asymmetry
2005, 16, 1889–1891; (j) Park, B.-M.; Mun, S.; Yun, J. Adv. Synth. Catal. 2006,