Ruthenium-diphosphine-catalyzed allylation of phenols: A gem-dialkyl-type effect induces high selectivity toward O-allylation

Organometallics

Volumn 28, Issue 24, 2009, Pages 7006-7014

  Van Rijn, Jimmy A ^a   Siegler, Maxime A ^b   Spek, Anthony L ^b   Bouwman, Elisabeth ^a   Drent, Eite ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOLS; ALLYLATION PRODUCTS; ALLYLATIONS; BIDENTATE CHELATES; BIDENTATE LIGANDS; BIDENTATE PHOSPHINES; BRIDGING GROUPS; CATALYST STRUCTURES; CATALYTIC PATHWAYS; CATALYTIC PERFORMANCE; CENTRAL ATOM; CYCLOPENTADIENYLS; DIAGNOSTIC TOOLS; DIPHOSPHINES; ELECTRONIC AND STRUCTURAL PROPERTIES; HIGH SELECTIVITY; HOMOGENEOUS CATALYSIS; KINETIC STABILITY; PHOSPHINE LIGANDS; PRECURSOR COMPLEXES; REACTION CONDITIONS; RUTHENIUM COMPLEXES;

CATALYSIS; CATALYSTS; CHELATION; DYES; ORGANIC POLYMERS; PHENOLS; PHOSPHORUS COMPOUNDS; REACTION INTERMEDIATES; REACTION KINETICS; RUTHENIUM; RUTHENIUM COMPOUNDS;

LIGANDS;

EID: 73549124306     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900832g     Document Type: Article

References (33)

1. Au, A. T.; Nafziger, J. L. Patent WO 9620232, 1996.
2. Bruneau, C.; Renaud, J. L.; Demerseman, B. Chem.-Eur. J 2006, 12, 5178-5187.
3. Zhang, H. J.; Demerseman, B.; Xi, Z. F.; Bruneau, C. Eur. J. Inorg. Chem. 2008, 3212-3217.
4. Onitsuka, K.; Okuda, H.; Sasai, H. Angew. Chem., Int. Ed. 2008, 47, 1454-1457.
5. Satoh, T.; Ikeda, M.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4877-4879.
6. Tada, Y.; Satake, A.; Shimizu, I.; Yamamoto, A. Chem. Lett. 1996, 1021-1022.
7. Nieves, I. F.; Schott, D.; Gruber, S.; Pregosin, P. S. Helv. Chim. Acta 2001, 90, 211-216.
8. van Rijn, J. A.; Lutz, M.; von Chrzanowski, L. S.; Spek, A. L.; Bouwman, E.; Drent, E. Adv. Synth. Catal. 2009, 351, 1637-1647.
9. Bruce, M. I.; Wong, F. S.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1981, 1398-1405.
10. Pearson, W. H.; Shade, J. E.; Brown, J. E.; Bitterwolf, T. E. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1996, 52, 1106-1110.
11. Aionso, A. G.; Reventos, L. B. J. Organomet. Chem. 1988, 338, 249-254.
12. Bruce, M. I.; Ellis, B. G.; Low, P. J.; Skelton, B. W.; White, A. H. Organometallics 2003, 22, 3184-3198.
13. van der Drift, R. C.; Bouwman, E.; Drent, E.; Kooijman, H.; Spek, A. L.; van Oort, A. B.; Mul, W. P. Organometallics 2002, 21, 3401-3407.
14. van Rijn, J. A.; Marques-Gallego, P.; Reedijk, J.; Lutz, M.; Spek, A. L.; Bouwman, E. Dalton Trans. 2009, DOI: 10.1039/b909520a.
15. Marcone, J. E.; Moloy, K. G. J. Am. Chem. Soc. 1998, 120, 8527-8528
16. Arthur, K. L.; Wang, Q. L.; Bregel, D. M.; Smythe, N. A.; O'Neill, B. A.; Goldberg, K. I.; Moloy, K. G. Organometallics 2005, 24, 4624-4628.
17. Mul, W. P.; van der Made, A. W.; Smaardijk, A. A.; Drent, E. In Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and Cooligomers; Sen, A., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 87-140.
18. Hewertson, W.; Watson, H. R. J. Chem. Soc. 1962, 1490-&.
19. Pons, A.; Rossell, O.; Seco, M.; Solans, X.; FontBardia, M. J. Organomet. Chem. 1996, 514, 177-182.
20. Kraihanzel, C. S.; Ressner, J. M.; Gray, G. M. Inorg. Chem. 1982, 21, 879-887.
21. Bianchini, C.; Lee, H. M.; Meli, A.; Moneti, S.; Vizza, F.; Fontani, M.; Zanello, P. Macromolecules 1999, 32, 4183-4193.
22. de Groot, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. Eur. J. Org. Chem. 2002, 1085-1095.
23. Schmidbaur, H.; Paschalidis, C.; Steigelmann, O.; Muller, G. Chem. Ber. 1989, 122, 1851-1855.
24. COLLECT; Nonius BV: Delft, The Netherlands, 1999.
25. Schreurs, A. M. M. PEAKREF; University of Utrecht: The Netherlands, 1999.
26. (26) Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Carter, C. W., Jr., Sweet, R. M., Eds.; Vol. 276: Macromolecular Crystallography, 1997; Part A, pp 307-326. (Pubitemid 27085611)
27. Duisenberg, A. J. M.; Kroon-Batenburg, L. M. J.; Schreurs, A. M. M. J. Appl. Crystallogr. 2003, 36, 220-229.
28. Beurkens, P. T.; Admiraal, G.; Beurkens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF99 Program System, Technical Report of the Crystallography Laboratory at University of Nijmegen; University of Nijmegen: Nijmegen, The Netherlands, 1999.
29. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122.
30. Sheldrick, G. M. SADABS, Version 2006/1; University of Göttingen: Germany, 2006.
31. Sheldrick, G. M. TWINABS, Version 1.05; University of Göttingen: Germany, 2003.
32. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13.
33. Duisenberg, A. J. M. J. Appl. Crystallogr. 1992, 25, 92-96.