Room temperature asymmetric Pd-catalyzed methoxycarbonylation of norbornene: Highly selective catalysis and HP-NMR studies

Dalton Transactions

Volumn 41, Issue 23, 2012, Pages 6980-6991

  Blanco, Carolina ^a   Godard, Cyril ^a   Zangrando, Ennio ^b   Ruiz, Aurora ^a   Claver, Carmen ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SPECIES; BIDENTATE PHOSPHINES; CATALYST PRECURSORS; CATALYTIC CONDITIONS; CATALYTIC SYSTEM; DIPHOSPHINES; HIGH SELECTIVITY; METHOXYCARBONYLATION; MONODENTATES; NORBORNENES; PALLADIUM COMPLEXES; PROTONATED; ROOM TEMPERATURE;

CATALYSIS; ESTERIFICATION; ESTERS; METHANOL; PALLADIUM COMPOUNDS; PHOSPHORUS COMPOUNDS; PROTONATION;

LIGANDS;

2 NORBORNENE; 2-NORBORNENE; CARBON MONOXIDE; NORBORNANE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRESSURE; TEMPERATURE;

CARBON MONOXIDE; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; NORBORNANES; PALLADIUM; PRESSURE; SUBSTRATE SPECIFICITY; TEMPERATURE;

EID: 84862186842     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/c2dt30267e     Document Type: Article

References (52)

1. R. I. Pugh E. Drent Adv. Synth. Catal. 2002 344 837
2. E. Drent P. H. M. Budzelaar Chem. Rev. 1996 96 663
3. C. Bianchini A. Meli W. Oberhauser Dalton Trans. 2003 2627
4. I. del Río C. Claver P. W. M. N. van Leeuwen Eur. J. Inorg. Chem. 2001 2719
5. A. Sen, in Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and Cooligomers, ed., A. Sen, Kluwer, Dordrecht, vol. 27, 2003
6. K. Gabor Chem. Rev. 2001 101 3435
7. G. R. Eastham, R. P. Tooze, X. L. Wang and K. Whiston, Int. Pat., 9619434, 1996
8. C. Godard, A. Ruiz, M. Diéguez, O. Pàmies and C. Claver, in Catalytic Asymmetric Synthesis, ed., I. Ojima, Wiley, 3rd edn, 2010, p. 799
9. E. Guiu M. Caporali B. Muñoz C. Müller M. Lutz A. L. Spek C. Claver P. W. N. M. van Leeuwen Organometallics 2006 25 3102
10. C. Bianchini A. Meli Coord. Chem. Rev. 2002 225 35
11. C. Bianchini H. M. Lee G. Mantovani A. Meli W. Oberhauser New J. Chem. 2002 26 387
12. C. Bianchini G. Mantovani A. Meli W. Oberhauser P. Brugeller T. Stampfl J. Chem. Soc., Dalton Trans. 2001 690
13. J. K. Liu B. T. Heaton J. A. Iggo R. Whyman Angew. Chem., Int. Ed. 2004 43 90
14. W. Clegg G. R. Eastham M. R. J. Elsegood B. T. Heaton J. A. Iggo R. P. Tooze R. Whyman S. Zacchini J. Chem. Soc., Dalton Trans. 2002 3300
15. W. Clegg G. R. Eastham M. R. J. Elsegood B. T. Heaton J. A. Iggo R. P. Tooze R. Whyman S. Zacchini Organometallics 2002 21 1832
16. B. K. Muñoz E. Santos C. Godard E. Zangrando C. Bo A. Ruiz C. Claver Eur. J. Inorg. Chem. 2008 4625
17. G. R. Eastham, R. P. Tooze, M. Kilner, D. F. Foster and D. J. Cole-Hamilton, J. Chem. Soc., Dalton Trans., 2002, 1613
18. P. W. N. M. van Leeuwen M. A. Zuideveld B. H. G. Swennenhuis Z. Freixa P. C. J. Kamer K. Goubitz J. Fraanje M. Lutz A. N. Spek J. Am. Chem. Soc. 2003 125 5523
19. G. R. Eastham B. T. Heaton J. A. Iggo R. P. Tooze R. Whyman S. Zacchini Chem. Commun. 2000 609
20. V. de la Fuente M. Waugh G. R. Eastham J. A. Iggo S. Castillón C. Claver Chem.-Eur. J. 2010 16 23 6919
21. Y. Kawashima K. Okano K. Nozaki T. Hiyama Bull. Chem. Soc. Jpn. 2004 77 347
22. B. K. Muñoz C. Godard A. Marinetti A. Ruiz J. Benet-Buchholz C. Claver Dalton Trans. 2007 5524
23. C. Botteghi G. Consiglio P. Pino Chimia 1973 27 477
24. T. Hayashi M. Tanaka I. Ogata Tetrahedron Lett. 1978 19 3925
25. T. Hayashi M. Tanaka I. Ogata J. Mol. Catal. 1984 26 17
26. J. Gironés J. Duran A. Polo J. Real Chem. Commun. 2003 1776
27. C. Blanco A. Ruiz C. Godard A. Marinetti N. Fleury-Brégeot C. Claver Adv. Synth. Catal. 2009 351 1813
28. S. Oi M. Nomura T. Aiko Y. Inoue J. Mol. Catal. A: Chem. 1997 115 289
29. H. Zhou S. Lu J. Hou H. Chen H. Fu H. Wang Chem. Lett. 1996 339
30. J. Hou H. Zhou L. Chen Q. Ou Anal. Lett. 1996 29 15 2755
31. G. Fráter J. A. Bajgrowicz P. Kraft Tetrahedron 1998 54 7633
32. G. Buchbauer I. Stappen C. Pretterklieber P. Wolschann Eur. J. Med. Chem. 2004 39 1039
33. W. Clegg G. R. Eastham M. R. J. Elsegood R. P. Tooze X. L. Wang K. Whiston Chem. Commun. 1999 1877
34. K. Kudo M. Hidal T. Murayama Y. Uchida J. Chem. Soc. D 1970 1701b 1702
35. J. Grévin P. Kalck J. Organomet. Chem. 1994 476 c23
36. K. Nozaki M. L. Kantam T. Horiuchi H. Takaya J. Mol. Catal. A: Chem. 1997 118 247
37. W. de Graaf J. Boersma G. van Koten C. J. Elsevier J. Organomet. Chem. 1989 378 115
38. B. Sesto G. Consiglio Chem. Commun. 2000 1011
39. A. Voituriez A. Panossian N. Fleury-Brégeot P. Retailleau A. Marinetti Adv. Synth. Catal. 2009 351 1968
40. R. J. Cross A. R. Kennedy K. W. Muir J. Organomet. Chem. 1995 487 227
41. F. Bachechi Struct. Chem. 2003 14 263
42. R. J. Cross A. R. Kennedy K. W. Muir J. Organomet. Chem. 1995 487 227
43. C. W. McFarlane R. F. M. White J. Chem. Soc. D 1969 744
44. G. A. Olah C. W. McFarlane J. Org. Chem. 1969 34 1832
45. P. Leoni M. Sommovigo M. Pasquali S. Midollini D. Braga P. Sabatino Organometallics 1991 10 1038
46. M. Portnoy D. Milstein Organometallics 1994 13 600
47. R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, New York, 1985, p. 59
48. M. S. Kharasch R. C. Seyler F. R. Mayo J. Am. Chem. Soc. 1938 60 882
49. D. Drew J. R. Doyle Inorg. Synth. 1972 13 47
50. Z. Otwinowski and W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode, in Methods in Enzymology, ed., C. W. Carter Jr., and, R. M. Sweet, Academic Press, New York, 1997, vol. 276, pp. 307 326
51. G. M. Sheldrick, SHELX97 Programs for Crystal Structure Analysis (Release 97-2), University of Göttingen, Germany, 1998
52. L. J. Farrugia J. Appl. Crystallogr. 1999 32 837