An improved synthesis of functionalized biphenyl-based phosphine ligands

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5334-5341

  Tomori, Hiroshi ^a   Fox, Joseph M ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BIPHENYL DERIVATIVE; LIGAND; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; PURIFICATION; REACTION ANALYSIS; SYNTHESIS;

BIPHENYL COMPOUNDS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHINES; SPECTROPHOTOMETRY, INFRARED;

EID: 0034714545     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000691h     Document Type: Article

References (73)

1. For reviews on Pd-catalyzed animation, see (a) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
2. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
3. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
4. Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Ch. 2.
5. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
6. For other reports on the amination reactions of aryl chlorides, see (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
7. (b) Yamamoto, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367.
8. (c) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807.
9. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
10. (e) Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237.
11. (f) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Peterson, J. L. Organometallics 1999, 18, 1840.
12. (g) Riermeier, T. H.; Zapf, A.; Beller, M. Top. Catal. 1997, 4, 301, and references therein.
13. (h) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
14. 3, see (i) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
15. For other reports on the Suzuki reactions of aryl chlorides, see (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
16. (b) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
17. (c) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. J. Organomet. Chem. 1998, 557, 93.
18. (d) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348.
19. (e) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
20. (f) Zhang, C.; Trudell, M. L. Tetrahedron Lett. 2000, 41, 595.
21. (g) Shen, W. Tetrahedron Lett. 1997, 38, 5575.
22. (h) Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985.
23. (i) Bei, X.; Turner, H. W.; Weinberg, H.; Guram, A. S.; Peterson, J. L. J. Org. Chem. 1999, 64, 6797.
24. (j) Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855.
25. (k) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
26. For earlier reports on the Pd-catalyzed intermolecular α-arylation of ketones, see (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
27. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
28. (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
29. (d) Hou, D.; Mas, J. L. U.S. Patent, 4992591, 1991. Chem. Abstr. 1991, 115, 28927z. For more recent reports,
30. see ref 12, and (e) Satoh, T.; Inoh, J.-i.; Kawamura, Y.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 2239.
31. (f) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
32. For the asymmetric Pd-catalyzed α-arylation of ketones, see (a) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918.
33. For the Pd-catalyzed asymmetric α-vinylation of ketones, see (b) Chieffi, A.; Kamikawa, K.; Åhman, J.; Buchwald, S. L., submitted.
34. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
35. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
36. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
37. Ligands 1, 3, and 4 are commercially available from Strem Chemical Co.
38. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
39. Old, D. W.; Harris, M. C.; Buchwald, S. L. Org. Lett., in press.
40. For other reports on the Pd-catalyzed formation of N-aryl indoles, see ref 4i, and Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
41. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
42. For an additional report on the Pd-catalyzed formation of diaryl ethers, see: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
43. The formation of biphenyls from arylmetals and benzyne dates back to experiments that were conducted in a retort by Fittig: (a) Fittig, R. Ann. 1864, 132, 202.
44. For a discussion of the history of benzyne chemistry, see pp 1-8 of (b) Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
45. For reviews, see Ch 2 of ref 17b and (a) Sharp, J. T. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Stoddart, J. F., Eds., Pergamon Press: Oxford, 1979; Vol. 1, p 455.
46. (b) Gilchrist, T. L. In The Chemistry of Functional Groups; Patai, S., Rappoport, Z., Eds., Wiley: Chichester, 1983, Suppl. C, part 1, Chapter 11.
47. (c) Grundmann, C. In Methoden der Organischen. Chemie (Houben-Weyl); MÜller, E., Bayer, O., Ed., Thieme: Stuttgart, New York, 1981, Board 5/2b, pp 613-515.
48. (d) Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds., Pergamon Press: Oxford, 1991; Vol. 4, Chapter 2.3.
49. (e) Huisgen, R.; Sauer, J. Angew. Chem. 1960, 72, 91.
50. (a) Wittig, G.; Pieper, G.; Fuhrmann, G. Chem. Ber. 1940, 73, 1193.
51. (b) Wittig, G.; Merkle, W. Chem. Ber. 1942, 75, 1491.
52. (c) Huisgen, R.; Rist, H. Liebigs Ann. Chem. 1955, 594, 137.
53. (d) Wittig, G.; Pohmer, L. Chem. Ber. 1956, 89, 1334.
54. (a) Wittig, G.; Fuhrmann, G. Chem. Ber. 1940, 73, 1197.
55. (b) Hellwinkel, D. Chem. Ber. 1966, 99, 3642.
56. (c) Hellwinkel, D.; Knabe, B. Chem. Ber. 1971, 104, 1761.
57. (d) Hellwinkel, D.; Reiff, G.; Nykodym, V. Liebigs Ann. Chem. 1977, 1013.
58. (e) Hart, H.; Harada, K.; Du, C.-J. F. J. Org. Chem. 1985, 50, 3104.
59. 23
60. Gilman, H.; Gorsich, R. D. J. Am. Chem. Soc. 1956, 78, 2217.
61. (a) Vinod, T.; Hart, H. J. Org. Chem. 1990, 55, 881.
62. (b) Grewal, R. S.; Hart, H.; Vinod, T. J. Org. Chem. 1992, 57, 2721.
63. (c) Hart, H.; Rajakumar, P. Tetrahedron 1993, 51, 1313.
64. Bartle, K. D.; Heaney, H.; Jones, D. W.; Lees, P. Tetrahedron 1965, 21, 3289.
65. See Ch 1 of ref 17b. For a specific example, see Wittig, G. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 964.
66. Wittig and Pohmer compared the reactions of o-fluorophenylmagnesium bromide and o-chlorophenylmagnesium bromide with furan in refluxing THF. After 1 h and treatment with 5 N HCl, the former reaction produced α-naphthol in 54% yield and gave no fluorobenzene; the latter reaction gave α-naphthol in 11% yield and chlorobenzene in 55% yield. After 5 weeks, 1,4-dihydronaphthalene-1,4-endoxide was isolated in 40% yield from the latter reaction. See ref 19d.
67. (a) Du, C.-J. F.; Hart, H.; Ng, K.-K. D. J. Org. Chem. 1986, 51, 3162.
68. (b) Ghosh, T.; Hart, H. J. Org. Chem. 1988, 53, 3555.
69. (c) Saednya, A.; Hart, H. Synthesis 1996, 1455.
70. The formation of terphenyls from the reaction of 2 equiv of benzyne with 1 equiv of an arylmetal is well-known. For examples, see refs 22, 24, and Wittig, G.; Hellwinkel, D. Chem. Ber. 1964, 97, 769.
71. Lai, Y.-H. Synthesis 1981, 585.
72. 15
73. The formation of 2-dimethylaminophenylmagnesium chloride was monitored by taking aliquots from the reaction mixture, quenching them with methanol, and analyzing them by GC. The preparation of 2-dimethylaminophenylmagnesium chloride was most efficient when dibromoethane was added to the 2-chloro-N,N-dimethylaniline and magnesium dropwise over the course of 1-1.5 h. The formation of the Grignard reagent was more sluggish when the dibromoethane was added in one portion to the 2-chloro-N,N-dimethylaniline and magnesium, or when the dibromoethane was added to the magnesium prior to the addition of 2-chloro-N,N-dimethylaniline.