Solvent-induced reduction of palladium-aryls, a potential interference in pd catalysis

Organometallics

Volumn 32, Issue 19, 2013, Pages 5428-5434

  Molina De La Torre, Jesús A ^a   Espinet, Pablo ^a   Albéniz, Ana C ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,4-DIOXANE; CYCLOHEXANONES; DECOMPOSITION MECHANISM; DIFFERENT SOLVENTS; HIGH TEMPERATURE; POTENTIAL INTERFERENCES; RE-OXIDATION; REDUCTION PRODUCTS;

AMIDES; DECOMPOSITION; ETHERS; KETONES; ORGANIC SOLVENTS; SOLVENTS;

PALLADIUM COMPOUNDS;

EID: 84885586174     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om400713y     Document Type: Article

References (57)

1. Metal Catalyzed Cross-Coupling Reactions; Meijere, A. Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
2. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley-VCH: Weinheim, 2004.
3. Legros, J. Y.; Primault, G.; Toffano, M.; Rivière, M. A.; Fiaud, J. C. Org. Lett. 2000, 2, 433-436
4. Martins, A.; Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 5186-5188
5. Lau, S. Y. W.; Andersen, N. G.; Keay, B. A. Org. Lett. 2001, 3, 181-184
6. Zawisza, A. M.; Ganchegui, B.; González, I.; Bouquillon, S.; Roglans, A.; Hénin, F.; Muzart, J. J. Mol. Catal. A: Chem. 2008, 283, 140-145
7. Deng, Y.; Persson, A. K.; Bäckvall, J.-E. Chem.-Eur. J. 2012, 18, 11498-11523
8. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
9. Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170-1214
10. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780-1824
11. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
12. Espinet, P.; Albéniz, A. C.; Casares, J. A.; Martínez- Ilarduya, J. M. Coord. Chem. Rev. 2008, 252, 2180-2208
13. Albéniz, A. C.; Espinet, P.; Jeannin, Y.; Philoche-Levisalles, M.; Mann, B. J. Am. Chem. Soc. 1990, 112, 6594-6600 (Heck-type processes)
14. Casado, A. L.; Espinet, P.; Gallego, A. M.; Martínez-Ilarduya, J. M. Chem. Commun. 2001, 339-340 (Stille reaction)
15. Pérez-Temprano, M. H.; Nova, A.; Casares, J. A.; Espinet, P. J. Am. Chem. Soc. 2008, 130, 10518-10520 (Sn-Pd transmetalation)
16. Albéniz, A. C.; Espinet, P.; Martín-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504-11505
17. Albéniz, A. C.; Espinet, P.; Martín-Ruiz, B.; Milstein, D. Organometallics 2005, 24, 3679-3684
18. Zhang, X.; Fan, S.; He, C.-Y.; Wan, X.; Min, Q.-Q.; Yang, J.; Jiang, Z.-X. J. Am. Chem. Soc. 2010, 132, 4506-4507
19. Martínez-Arranz, S.; Carrera, N.; Albéniz, A. C.; Espinet, P.; Vidal-Moya, A. Adv. Synth. Catal. 2012, 354, 3551-3560
20. Carrera, N.; Gutiérrez, E.; Benavente, R.; Villavieja, M. M.; Albéniz, A. C.; Espinet, P. Chem.-Eur. J. 2008, 14, 10141-10148
21. Usón, R.; Forniés, J.; Nalda, J. A.; Lozano, M. J.; Espinet, P.; Albéniz, A. C. Inorg. Chim. Acta 1989, 156, 251
22. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009-4091
23. Chen, J.; Zhang, Y.; Yang, L.; Zhang, X.; Liu, J.; Li, L.; Zhang, H. Tetrahedron 2007, 63, 4266-4270
24. Viciu, M. S.; Grasa, G. A.; Nolan, S. P. Organometallics 2001, 20, 3607-3612
25. Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620
26. Mueller, J. A.; Goller, C. P.; Sigman, M. S. J. Am. Chem. Soc. 2004, 126, 9724-9734
27. Albéniz, A. C.; Espinet, P.; Lin, Y.-S. Organometallics 1997, 16, 4030-4032
28. The use radical traps in these experiments has no conclusive value in this case since we have shown that they react with palladium hydrides: Albéniz, A. C.; Espinet, P.; López-Fernández, R.; Sen, A. J. Am. Chem. Soc. 2002, 124, 11278-11279
29. Ding, S.; Jiao, N. Angew. Chem., Int. Ed. 2012, 51, 9226-9237
30. Muzart, J. Tetrahedron 2009, 65, 8313-8323
31. Wan, Y.; Alterman, M.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6232-6235
32. Serp, P.; Hernández, M.; Richard, B.; Kalck, P. Eur. J. Inorg. Chem. 2001, 2327-2336
33. Zawisza, A. M.; Muzart, J. Tetrahedron Lett. 2007, 48, 6738-6742
34. Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626-3633
35. Logan, M. E.; Oinen, M. E. Organometallics 2006, 25, 1052-1054
36. Rajagopal, S.; Spatola, A. F. J. Org. Chem. 1995, 60, 1347-1355
37. Ben-David, Y.; Gozin, M.; Portnoy, M.; Milstein, D. J. Mol. Catal. A: Chem. 1992, 73, 173-180
38. For a review, see: Muzart, J. Eur. J. Org. Chem. 2010, 3779-3790
39. Muzart, J.; Pète, J.-P. J. Mol. Catal. 1982, 15, 373-376
40. Theisen, R. J. J. Org. Chem. 1971, 36, 752-757
41. Trost, B. M.; Metzner, P. J. J. Am. Chem. Soc. 1980, 102, 3572-3577
42. Wenzel, T. T. J. Chem. Soc., Chem. Commun. 1989, 932-933
43. Diao, T.; Pun, D.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 8205-8212
44. Diao, T.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 14566-14569
45. Tokunaga, M.; Harada, S.; Iwasawa, T.; Obora, Y.; Tsuji, Y. Tetrahedron Lett. 2007, 48, 6860-6862
46. Izawa, Y.; Pun, D.; Stahl, S. S. Science 2011, 333, 209-213
47. Pun, D.; Diao, T.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 8213-8221
48. Cermola, F.; Iesce, M. R. J. Org. Chem. 2002, 67, 4937-4944
49. Silverman, S. K.; Foote, C. S. J. Am. Chem. Soc. 1991, 113, 7672-7675
50. Gligorich, K. M.; Sigman, M. S. Angew. Chem., Int. Ed. 2006, 45, 6612-6615
51. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420
52. Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212-10213
53. Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188-7189
54. Mimoun, H.; Charpentier, R.; Mitschler, A.; Fischer, J.; Weiss, R. J. Am. Chem. Soc. 1980, 102, 1047-1054
55. Wayland, B. B.; Schramm, R. F. Inorg. Chem. 1969, 8, 971-976
56. Harris, C. M.; Livingstone, S. E.; Stephenson, N. C. J. Chem. Soc. 1958, 3697-3702
57. Usón, R.; Forniés, J.; Martínez, F.; Tomás, M. J. Chem. Soc., Dalton Trans. 1980, 888-894