Transfer semihydrogenation of alkynes catalyzed by a zero-valent palladium N-heterocyclic carbene complex

Angewandte Chemie - International Edition

Volumn 47, Issue 17, 2008, Pages 3223-3226

  Hauwert, Peter ^a   Maestri, Giovanni ^b   Sprengers, Jeroen W ^a   Catellani, Marta ^b   Elsevier, Cornelis J ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Alkynes; Carbene ligands; Hydrogen transfer; Hydrogenation; Palladium

Indexed keywords

ACETYLENE; CATALYSIS; CHEMICAL REACTIONS; HYDROCARBONS; HYDROGEN; HYDROGENATION; KETONES; OLEFINS; ORGANIC COMPOUNDS; PALLADIUM; PALLADIUM COMPOUNDS; PARAFFINS;

ALKYNES; CARBENE LIGANDS; CHEMICAL EQUATIONS; HYDROGEN GASES; HYDROGEN TRANSFER; N-HETEROCYCLIC CARBENE COMPLEXES; N-HETEROCYCLIC CARBENE LIGAND; SEMIHYDROGENATION; TRANSFER HYDROGENATIONS; Z ALKENES;

CATALYST SELECTIVITY;

EID: 53549092110     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705638     Document Type: Article

References (31)

1. D. Klomp, U. Hanefeld, J. A. Peters in Handbook for Homogeneous Hydrogenation, Vol. 2, 1st ed. (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007, p. 585.
2. For reviews on transfer hydrogenation, see: a) S. Gladiali, E. Alberico, Chem. Soc. Rev. 2006, 35, 226;
3. b) J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev. 2006, 35, 237;
4. c) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97.
5. a) A. C. Hillier, H. M. Lee, E. D. Stevens, S. P. Nolan, Organometallics 2001, 20, 4246;
6. b) X. Wu, J. Xiao, Chem. Commun. 2007, 2447;
7. c) R. Corberán, M. Sanaú, E. Peris, Organometallics 2007, 26, 3492;
8. d) S. Enthaler, R. Jackstell, B. Hagemann, K. Junge, G. Erre, M. Beller, J. Organomet. Chem. 2006, 691, 4652.
9. a) S. Kuhl, R. Schneider, Y. Fort, Organometallics 2003, 22, 4184;
10. b) J. S. M. Samec, A. H. Éll, J. B. Åberg, T. Privalov, L. Eriksson, J.-E. Bäckvall, J. Am. Chem. Soc. 2006, 128, 14293;
11. c) M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal. 2007, 349, 1555.
12. a) D. Gnanamgari, A. Moores, E. Rajaseelan, R. H. Crabtree, Organometallics 2007, 26, 1226;
13. b) A. G. Campaña, R. E. Estévez, N. Fuentes, R. Robles, J. M. Cuerva, E. Buñuel, D. Cárdenas, J. E. Oltra, Org. Lett. 2007, 9, 2195.
14. a) Y. Gao, M. C. Jennings, R. J. Puddephatt, Can. J. Chem. 2001, 79, 915;
15. b) K. Tani, A. Iski, T. Yamagata, Chem. Commun. 1999, 1821.
16. K. Tani, N. Ono, S. Okamoto, F. Sato, J. Chem. Soc. Chem. Commun. 1993, 386.
17. a) A. M. Kluwer, C. J. Elsevier in Handbook for Homogeneous Hydrogenation, Vol. 1, 1st ed. (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007, p. 375;
18. b) J.W. Sprengers, J. Wassenaar, N. D. Clement, K. J. Cavell, C. J. Elsevier, Angew. Chem. 2005, 117, 2062;
19. Angew. Chem. Int. Ed. 2005, 44, 2026;
20. c) F. Alonso, I. Osante, M. Yus, Tetrahedron 2007, 63, 93;
21. d) A. M. Kluwer, T. S. Koblenz, T. Jonischkeit, K. Woelk, C. J. Elsevier, J. Am. Chem. Soc. 2005, 127, 15470;
22. e) M. W. E. van Laren, C. J. Elsevier, Angew. Chem. 1999, 111, 3926;
23. Angew. Chem. Int. Ed. 1999, 38, 3715.
24. a) H. Lindlar, Helv. Chim. Acta 1952, 35, 446;
25. b) A. Molnár, A. Sárkány, M. Varga, J. Mol. Catal. A 2001, 173, 185.
26. a) N. D. Clement, K. J. Cavell, L.-L. Ooi, Organometallics 2006, 25, 4155;
27. b) K. J. Cavell, D. J. Stufkens, K. Vrieze, Inorg. Chim. Acta 1981, 47, 67.
28. For reviews on N-heterocyclic carbenes, see: a) W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
29. Angew. Chem. Int. Ed. 2002, 41, 1290;
30. b) R. H. Crabtree, J. Organomet. Chem. 2005, 690, 5451;
31. c) N. M. Scott, S. P. Nolan, Eur. J. Inorg. Chem. 2005, 1815.