Highly efficient nickel-catalyzed cross-coupling of succinic and glutaric anhydrides with organozinc reagents

Journal of the American Chemical Society

Volumn 127, Issue 1, 2005, Pages 247-254

  Bercot, Eric A ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; MOLECULAR DYNAMICS; NICKEL; OLEFINS; OXIDATION; STYRENE; SUBSTRATES;

ARYLZINC REAGENTS; GLUTARIC ANHYDRIDES; MOLECULAR COMPLEXITY; REACTION RATE;

ALKYLATION;

ALKENE; GLUTARIC ACID DERIVATIVE; GLUTARIC ANHYDRIDE; NICKEL; STYRENE; SUCCINIC ANHYDRIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; OXIDATION;

EID: 11844278498     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044588b     Document Type: Article

References (83)

1. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998.
2. (a) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
3. (b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
4. For a review see: Dieter, R. K. Tetrahedron 1999, 55, 4177-4236.
5. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
6. The direct addition of main-group organometallics to acid halides is well-known, see: Shirley, D. A. Org. React. 1954, 8, 28-58.
7. Kosugi, M.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 1423-1424.
8. (a) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636-3638.
9. (b) Milstein, D.; Stille, J. K. J. Org. Chem. 1979, 44, 1613-1618.
10. (a) Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T.Tetrahedron Lett. 1998, 39, 3189-3192.
11. (b) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261.
12. (c) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S.; Org. Lett. 2003, 5, 3033-3035.
13. Kakino, R.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 371-376.
14. (a) Jabri, N.; Alexakis, A.; Normant, J. F. Tetrahedron 1986, 42, 1369-1380.
15. (b) Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 2316-2317.
16. (c) Cacchi, S.; Fabrizi, G.; Gavazza, F.; Goggiamani, A. Org. Lett. 2003, 5, 289-291.
17. (d) Wang, D.; Zhang, Z. Org. Lett. 2003, 5, 4645-4648.
18. (e) Yamane, M.; Uera, K.; Narasaka, K. Chem. Lett. 2004, 33, 424-425.
19. (f) Kazmierski, I.; Bastienne, M.; Gosmini, C.; Paris, J.-M.; Perichon, J. J. Org. Chem. 2004, 69, 936-942.
20. (a) Goossen, L. J.; Ghosh, K. Angew. Chem., Int. Ed. 2001, 40, 3458-3460.
21. (b) Goossen, L. J.; Ghosh, K. Eur. J. Org. Chem. 2002, 19, 3254-3267.
22. (a) Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 1333-1345.
23. (b) Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137-148.
24. (c) Yamamoto, A. J. Organomet. Chem. 2002, 653, 5-10.
25. For an excellent review see: Csende, F.; Stájer, G. Heterocycles 2000, 53, 1379-1419.
26. (a) Spivey, A. C.; Andrews, B. I. Angew. Chem., Int. Ed. 2001, 40, 3131-3134.
27. (b) For a review on alcoholysis of meso anhydrides, see: Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965-2983.
28. (a) Fieser, L. F.; Seligman, A. M. J. Am. Chem. Soc. 1938, 60, 170-176.
29. (b) Ranu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380-6386.
30. (c) Seed, A. J.; Sonpatki, V.; Herbert, M. R. Org. Synth. 2002, 79, 204-208.
31. (a) Canonne, F.; Akssira, M. Tetrahedron 1985, 41, 3695-3704.
32. (b) For the diastereoselective addition of aryl Grignard reagents to cyclic anhydrides, see: Real, S. D.; Kronenthal, D. R., Wu, H. Y. Tetrahedron Lett. 1993, 34, 8063-8066.
33. (c) For the addition of alkyl aluminum halides to anhydrides, see: Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242-2248.
34. Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1057-1059.
35. (a) Bercot, E. A.; Rovis, T. J. Am Chem. Soc. 2002, 124, 174-175.
36. (b) It was subsequently found that palladium catalysts participate in this type of reaction manifold, culminating in the discovery of a catalytic enantioselective anhydride alkylation proceeding with uniformly high selectivities: Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 10248-10249.
37. (a) Sano, K.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1983, 115-118.
38. (b) Sano, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 7, 2741-2747.
39. (c) Yamamoto, T.; Sano, K.; Yamamoto, A. J. Am. Chem. Soc. 1987, 109, 1092-1100.
40. (d) Castaño, A. M.; Echavarren, A. M. Tetrahedron Lett. 1990, 31, 4783-4786.
41. (e) Castaño, A. M.; Echavarren, A. M. Tetrahedron Lett. 1993, 34, 4361-4362.
42. (a) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473.
43. (b) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
44. (c) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890-3908.
45. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188.
46. The addition of arylzinc halides to maleic anhydride occurs at slightly elevated temperatures, see: Tarbell, D. S. J. Am. Chem. Soc. 1938, 60, 215-216.
47. Giovannini, R.; Studemann, T.; Dussin, G.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1998, 37, 2387-2390.
48. Toto, S. D.; Doi, J. T. J. Org. Chem. 1987, 52, 4999-5003.
49. (a) Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc. 1971, 93, 3350-3359.
50. (b) Yamamoto, T.; Abla, M.; Murakami, Y. Bull. Chem. Soc. Jpn. 2002, 75, 1997-2009.
51. Giovannini, R.; Studemann, T.; Devasagayaraj, A.; Dussin, G.; Knochel, P. J. Org. Chem. 1999, 64, 3544-3553.
52. (a) Giovannini, R.; Knochel, P. J. Am. Chem. Soc. 1998, 120, 11186-11187.
53. (b) Piber, M.; Jensen, A. E.; Rottlander, M.; Knochel, P. Org. Lett. 1999, 1, 1323-1326.
54. (c) Jensen, A. E.; Knochel, P J. Org. Chem. 2002, 67, 79-85.
55. Reaction times were determined by the disappearance of starting material as observed by TLC. Each reaction was assayed every 5 min for the first 30 min, then every 30 min for an additional 3 h. After 3 h each reaction was assayed every 6 h to an ultimate time of 42 h.
56. Reactions that are sluggish often result in the formation of ester byproducts presumably arising from the slow oxidation of the alkyl zinc reagent by adventitious oxygen; for a similar example, see: Katritzky, A. R.; Luo, Z. Heterocydes 2001, 55, 1467-1474.
57. On the basis of our previous report, trifluorotoluene seems to be an effective promoter if used in higher concentration (30 mol % trifluorotoluene and 1 mol % catalyst).
58. Schueler, P. E.; Rhodes, Y. E. J. Org. Chem. 1974, 39, 2063-2069.
59. Qualitative observations suggest bpy is the generally preferred ligand for succinic anhydrides and pyphos is the preferred ligand for glutaric anhydrides.
60. Currently, alkenyl and alkynyl zinc reagents are beyond the scope of this transformation.
61. It should be noted that generation of aryllithium reagents from aryl iodides by treatment with n-butyllithium leads to no observed product.
62. 2 was used for consistency in our studies regarding the substrate scope.
63. Alkyl-transition metal intermediates arising from alkyl or aryl group transfer from a main-group organometallic have been invoked in related reaction manifolds; see: (a) Bogdanovic, B.; Schwickardi, M. Angew. Chem., Int. Ed. 2000, 39, 4610-4612. (b) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609-612. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. (d) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844.
64. Alkyl-transition metal intermediates arising from alkyl or aryl group transfer from a main-group organometallic have been invoked in related reaction manifolds; see: (a) Bogdanovic, B.; Schwickardi, M. Angew. Chem., Int. Ed. 2000, 39, 4610-4612. (b) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609-612. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. (d) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844.
65. Alkyl-transition metal intermediates arising from alkyl or aryl group transfer from a main-group organometallic have been invoked in related reaction manifolds; see: (a) Bogdanovic, B.; Schwickardi, M. Angew. Chem., Int. Ed. 2000, 39, 4610-4612. (b) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609-612. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. (d) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844.
66. Alkyl-transition metal intermediates arising from alkyl or aryl group transfer from a main-group organometallic have been invoked in related reaction manifolds; see: (a) Bogdanovic, B.; Schwickardi, M. Angew. Chem., Int. Ed. 2000, 39, 4610-4612. (b) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609-612. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. (d) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844.
67. O'Brien, E. M.; Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2003, 125, 10498-10499.
68. (a) Trost, B. M.; Chen, F. Tetrahedron Lett. 1971, 12, 2603-2607.
69. (b) Uhlig, V. E.; Fehske, G.; Nestler, B. Z. Z. Anorg. Allg. Chem. 1980, 465, 141-146.
70. (c) Komiya, S.; Yamamoto, A.; Yamamoto, T. Chem. Lett. 1981, 193-196.
71. (d) Schönecker, B.; Walther, D.; Fischer, R.; Nestler, B.; Bräunlich, G.; Eibisch, H.; Droescher, P. Tetrahedron Lett. 1990, 31, 1257-1260.
72. Fischer, R.; Walther, D.; Kempe, R.; Sieler, J.; Schönecker, B. J. Organomet. Chem. 1993, 447, 131-136.
73. (a) For the addition of Grignard reagents; see: Canonne, P.; Kassou, M.; Akssira, M. Tetrahedron Lett. 1986, 27, 2001-2004; Berrier, C.; Bonnaud, B.; Patoiseau, J. F.; Bigg, D. Tetrahedron 1991, 47, 9629-9640.
74. (a) For the addition of Grignard reagents; see: Canonne, P.; Kassou, M.; Akssira, M. Tetrahedron Lett. 1986, 27, 2001-2004; Berrier, C.; Bonnaud, B.; Patoiseau, J. F.; Bigg, D. Tetrahedron 1991, 47, 9629-9640.
75. (b) For the addition of enolates; see: Murray, W. V.; Wachter, M. P. J. Org. Chem. 1990, 55, 3424-3426.
76. (c) For Friedel-Crafts acylation; see: Hagishita, S.; Kuriyama, K. Bull. Chem. Soc. Jpn. 1982, 55, 3216-3224.
77. (a) Bloomfield, J. J.; Lee, S. L. J. Org. Chem. 1967, 32, 3919-3924.
78. (b) Cross, B. E.; Stewart, J. C. Tetrahedron Lett. 1968, 3589-3590.
79. (c) Bailey, D. M.; Johnson, R. E. J. Org. Chem. 1970, 35, 3574-3576.
80. (a) Bürgi, H. B.; Lehn, J. M.; Wipff, G. J. Am. Chem. Soc. 1974, 96, 1956-1957.
81. (b) Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1563-1572.
82. Kayser, M. M.; Morand, P. Tetrahedron Lett. 1979, 695-698.
83. 3 cross-coupling reactions, see: Refs 23 and 26.