H/D exchange at aromatic and heteroaromatic hydrocarbons using D 2O as the deuterium source and ruthenium dihydrogen complexes as the catalyst

Angewandte Chemie - International Edition

Volumn 46, Issue 13, 2007, Pages 2269-2272

  Prechtl, Martin H G ^a,b   Hölscher, Markus ^a   Ben David, Yehoshoa ^c   Theyssen, Nils ^b   Loschen, Rebekka ^a   Milstein, David ^c   Leitner, Walter ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

C H activation; Density functional calculations; H D exchange; Homogeneous catalysis; Ruthenium

Indexed keywords

CATALYSTS; DENSITY FUNCTIONAL THEORY; DEUTERIUM COMPOUNDS; RUTHENIUM COMPOUNDS;

C-H ACTIVATION; EXCHANGE PROCESSES; HETEROAROMATIC HYDROCARBONS; HOMOGENEOUS CATALYSIS;

AROMATIC HYDROCARBONS;

EID: 34250850884     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603677     Document Type: Article

References (27)

1. R. H. Morris, P. G. Jessop, Coord. Chem. Rev. 1992, 121, 155-284.
2. a) B. Chaudret, R. Poilblanc, Organometallics 1985, 4, 1722-1726;
3. b) S. Sabo-Etienne, B. Chaudret, Coord. Chem. Rev. 1998, 178-180, 381-407.
4. F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826-834.
5. a) J. T. Golden, R. A. Andersen, R. G. Bergman, J. Am. Chem. Soc. 2001, 123, 5837-5838;
6. b) S. R. Klei, J. T. Golden, T. D. Tilley, R. G. Bergman, J. Am. Chem. Soc. 2002, 124, 2092-2093;
7. c) S. R. Klei, T. D. Tilley, R. G. Bergman, Organometallics 2002, 21, 4905-4911;
8. d) M. R. Skaddan, C. M. Yung, R. G. Bergman, Org. Lett. 2004, 6, 11-13;
9. e) C. M. Yung, M. R. Skaddan, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 13 033-13 043.
10. A. F. Thomas, Deuterium Labelling in Organic Chemistry, Meridith Cooperation, New York, 1971.
11. T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper and Row, New York, 1987.
12. M. Yamamoto, Y. Yokota, K. Oshima, S. Matsubara, Chem. Commun. 2004, 1714-1715.
13. B. Rybtchinski, R. Cohen, Y. Ben-David, J. M. L. Martin, D. Milstein, J. Am. Chem. Soc. 2003, 125, 11 041-11 050.
14. a) C. P. Lenges, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1999, 121, 4385-4396;
15. b) B. McAuley, M. J. Hockey, L. P. Kingston, J. R. Jones, W. J. S. Lockley, A. N. Mather, E. Spink, S. P. Thompson, D. J. Wilkinson, J. Labelled Compd. Radiopharm. 2003, 46, 1191-1204;
16. c) J. Krüger, B. Manmontri, G. Fels, Eur. J. Org. Chem. 2005, 1402-1408;
17. d) Q.-X. Guo, B.-J. Shen, H.-Q. Guo, T. Takahashi, Chin. J. Chem. 2005, 23, 341-344.
18. D. Giunta, M. Holscher, C. W. Lehmann, R. Mynott, C. Wirtz, W. Leitner, Adv. Synth. Catal. 2003, 345, 1139-1145.
19. a) S. Busch, W. Leitner, Chem. Commun. 1999, 2305-2306;
20. b) M. H. G. Prechtl, Y. Ben-David, D. Giunta, S. Busch, Y. Taniguchi, W. Wisniewski, H. Görls, R. J. Mynott, N. Theyssen, D. Milstein, W. Leitner, Chem. Eur. J. 2006, DOI: 10.1002/ chem.200600897.
21. a) P. Foley, R. DiCosimo, G. M. Whitesides, J. Am. Chem. Soc. 1980, 102, 6713-6725;
22. b) G. M. Whitesides, M. Hackett, R. L. Brainard, J.-P. P. M. Lavalleye, A. F. Sowinski, A. N. Izumi, S. S. Moore, D. W. Brown, E. M. Staudt, Organometallics 1985, 4, 1819-1830;
23. c) C. Paal, W. Hartmann, Ber. Dtsch. Chem. Ges. 1918, 51, 711-737.
24. For a recent experimental and computational study on H-X bond activation (X = O and C), see S. L. Chatwin, M. G. Davidson, C. Doherty, S. M. Donald, R. F. R. Jazzar, S. A. Macgregor, G. J. McIntyre, M. F. Mahon, M. K. Whittlesey, Organometallics 2006, 25, 99-110.
25. [8] and Ir complexes: E. Ben-Ari, R. Cohen, M. Gandelman, L. J. W. Shimon, J. M. L. Martin, D. Milstein, Organometallics 2006, 25, 3190-3210.
26. C-H activation of arenes with subsequent H transfer to olefins has been described for Ru complexes: a) M. Lail, C. M. Bell, D. Conner, T. R. Cundari, T. B. Gunnoe, J. L. Petersen, Organometallics 2004, 23, 5007-5020;
27. b) H. Weissman, X.-P. Song, D. Milstein, J. Am. Chem. Soc. 2001, 123, 337-338.