Ar-F reductive elimination from palladium(II) revisited

Organometallics

Volumn 26, Issue 20, 2007, Pages 4997-5002

  Grushin, Vladimir V ^a   Marshall, William J ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; LIGANDS; NUCLEAR MAGNETIC RESONANCE; PYROLYSIS;

AR-F REDUCTIVE ELIMINATION; BUCHWALD'S LIGANDS; NONACTIVATED CONGENERS;

PALLADIUM COMPOUNDS;

EID: 34948853914     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700469k     Document Type: Article

References (67)

1. For selected reviews, see: Muci, A. K.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
2. Hartwig, J. F. Synlett 2006, 1283.
3. Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599.
4. The high demand for new reactions leading cleanly to Ar-F bond formation is largely driven by biological activity of selectively fluorinated organic molecules. "As many as 30-40% of agrochemicals and 20% of pharmaceuticals on the market are estimated to contain fluorine, including half of the top 10 drugs sold in 2005." Thayer, A. M. Chem. Eng. News 2006, 84, No. 23 (June 5), 15.
5. Balz, G.; Schiemann, G. Chem. Ber. 1927, 60, 1186.
6. 4c (a) Adams, D. J.; Clark, J. H. Chem. Soc. Rev. 1999, 28, 225.
7. (b) Langlois, B.; Gilbert, L.; Forat, G. Ind. Chem. Libr. 1996, 8, 244.
8. (c) Sun, H.; Dimagno, S. G. Angew. Chem., Int. Ed. 2006, 45, 2720.
9. Grushin, V. V. Chem.-Eur. J. 2002, 8, 1006.
10. Fraser, S. L.; Antipin, M. Yu.; Khroustalyov, V. N.; Grushin, V. V. J. Am. Chem. Soc. 1997, 119, 4769.
11. Pilon, M. C.; Grushin, V. V. Organometallics 1998, 17, 1774.
12. Marshall, W. J.; Thorn. D. L.; Grushin, V. V. Organometallics 1998, 17, 5427.
13. Flemming, J. P.; Pilon, M. C.; Borbulevitch, O. Ya.; Antipin, M. Yu.; Grushin, V. V. Inorg. Chim. Acta 1998, 280, 87.
14. Grushin, V. V. Angew. Chem., Int. Ed. 1998, 37, 994.
15. Grushin, V. V. Organometallics 2000, 19, 1888.
16. Roe, D. C.; Marshall, W. J.; Davidson, F.; Soper, P. D.; Grushin, V. V. Organometallics 2000, 19, 4575.
17. Grushin, V. V.; Marshall, W. J. Angew. Chem., Int. Ed. 2002, 41, 4476.
18. Marshall, W. J.; Grushin, V. V. Organometallics 2003, 22, 555.
19. Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398.
20. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 4632.
21. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644.
22. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2004, 126, 3068.
23. Macgregor, S. A.; Roe, D. C.; Marshall, W. J.; Bloch, K. M.; Bakhmutov, V. I.; Grushin, V. V. J. Am. Chem. Soc. 2005, 127, 15304.
24. Macgregor, S. A. Chem. Soc. Rev. 2007, 36, 67.
25. Macgregor, S. A.; Wondimagegn, T. Organometallics 2007, 26, 1143.
26. Marshall, W. J.; Grushin, V. V. Organometallics 2004, 23, 3343.
27. Marshall, W. J.; Grushin, V. V. Organometallics 2003, 22, 1591.
28. Grushin, V. U.S. Patent 7,202,388, 2007.
29. Hull, Anani, and Sanford have recently reported an interesting exotic example of fluorination of Ar-H bonds via cyclopalladation, followed by electrophilic cleavage of the Pd-C bond with N-fluoropyridinium reagents. This approach cannot allow the highly sought nucleophilic displacement of Cl, Br, and I of nonactivated haloarenes with fluoride by definition. Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134.
30. Yandulov, D. V.; Tran, N. T. J. Am. Chem. Soc. 2007, 129, 1342.
31. 3/BL: Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.
32. Terrier, F. Nucleophilic Aromatic Displacement: The Influence of the Nitro Group; VCH: New York, 1991.
33. Miller, J. Aromatic Nucleophilic Substitution; Elsevier: London 1968.
34. See, for example: (a) Finger, G. C.; Kruse, C. W. J. Am. Chem. Soc. 1956, 78, 6034.
35. (b) Aksenov, V. V.; Vlasov, V. M.; Moryakina, I. M.; Rodionov, P. P.; Fadeeva, V. P.; Chertok, V. S.; Yakobson, G. G. J. Fluorine Chem. 1985, 28, 73.
36. The starting iodo dimers were prepared by the literature methods: Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
37. Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. Organometallics 1996, 15, 2745.
38. 2: C, 52.7; H, 4.3. Found: C, 52.7; H, 4.3.
39. 3P ligands. In 3, the F trans to C interacts with one methyl group of one of the phosphines (2.21 Å) and two methyls of the other (2.53 and 2.54 Å). The same pattern is observed for 5 (2.49, 2.56, and 2.58 Å). In addition, 3 exhibits an intermolecular contact between the fluorine trans to P and an aromatic CH of another molecule of 3. In 5, this F atom interacts intramolecularly with one ortho H of each anisyl ligand (2.56 and 2.67 A), (b) Brammer, L.; Bruton, E. A.; Sherwood. P. Cryst. Growth Des. 2001, 1, 277.
40. 3 (3%), and BL (6%) in toluene was stirred in a Teflon reactor at 110°C (oil bath) for 2 days. Considering the low yield of PhF, the high basicity of the fluoride source, reaction conditions, and the fact that much finely dispersed Pd black was quickly formed in this reaction, we hesitate to assert Ph-F reductive elimination from a soluble PhPdF intermediate, although this path should not be ruled out.
41. (a) For a recent review, see: Berkenbusch, T. Sci. Synth. 2006, 25, 689.
42. (b) Takagi, K.; Hayama, N.; Okamoto, T. Chem. Lett. 1978, 191.
43. (c) Takagi, K.; Hayama, N.; Inokawa, S. Bull. Chem. Soc. Jpn 1980, 53, 3691.
44. (d) Tsou, T. T.; Kochi. J. K. J. Org. Chem. 1980, 45, 1930.
45. (e) Suzuki, H.; Kondo, A.; Ogawa, T. Chem. Lett. 1985, 411.
46. (f) Meyer, G.; Rollin, Y.; Perichon, J. Tetrahedron Lett. 1986, 27, 3497.
47. (g) Yang. S. H.; Li, C. S.; Cheng, C. H. J. Org. Chem. 1987, 52, 691.
48. (h) Bozell, J. J.; Vogt, C. E. J. Am. Chem. Soc. 1988, 110, 2655.
49. (i) Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844.
50. (j) Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890.
51. (k) Arvela, R. K.; Leadbeater, N. E. Synlett 2003, 1145.
52. (l) Toto, P.; Gesquiere, J.-C.; Cousaert, N.; Deprez, B.; Willand, N. Tetrahedron Lett. 2006, 47, 4973.
53. For Pd-promoted halide exchange in otherwise unreactive, pseudoaromatic 9-iodo-m-carborane, see: Marshall, W. J.; Young, R. J., Jr.; Grushin. V. V. Organometallics 2001, 20, 523.
54. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232.
55. Stambuli, J. P.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346.
56. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc 2003, 125, 13944.
57. Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 1533.
58. Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184.
59. 2.
60. (b) Yahav-Levi, A.; Goldberg, I.; Vigalok, A. J. Am. Chem. Soc. 2006, 128, 8710.
61. Macgregor, S. A. Unpublished results.
62. Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787.
63. Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504.
64. Mann, G.; Shelby. Q.; Roy, A. H.; Hartwig, J. F. Organometallics 2003, 22, 2775.
65. 2 core needed to enable formation of aryl-fluoride net reductive elimination product in quantifiable yields (10%) in reactions with both 17 and 18 at 60° over 22 h."
66. The logical fallacy, in which it is claimed that a premise is true only because it has not been proven false or that a premise is false only because it has not been proven true. See, for example: Copi, I. M.; Cohen, C. Introduction to Logic, 12th ed.; Prentice Hall: Upper Saddle River, NJ, 2004.
67. 26 for the synthesis of 1.