From the Design of a Chiral Lewis Acid Catalyst to Metal-Catalyzed Coupling Reactions

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3245-3249

  Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; NICKEL; PALLADIUM;

LEWIS ACID; METAL-CATALYZED COUPLED REACTIONS;

CATALYSTS;

BENZENE DERIVATIVE; CARBON; LEWIS ACID; METAL; NICKEL; PALLADIUM;

CATALYSIS; CHEMICAL BOND; CHIRALITY; COMPLEX FORMATION; REACTION ANALYSIS; REVIEW; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACIDS; BORON COMPOUNDS; CARBON; CATALYSIS; METALS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 2442567748     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049908o     Document Type: Review

References (70)

1. For an early overview, see: Narasaka, K. Synthesis 1991, 1-11.
2. Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VHC: New York, 2000; Vols. 1 and 2.
3. For computations that suggest a rotational barrier of 0.8-1.4 kcal/mol for aldehyde-Lewis acid complexes, see: LePage, T. J.; Wiberg, K. B. J. Am. Chem. Soc. 1988, 110, 6642-6650.
4. For a strategy for minimizing this conformational flexibility, see: Corey, E. J.; Lee, T. W. Chem. Commun. 2001, 1321-1329.
5. For reviews of borabenzene chemistry, see: (a) Herberich, G. E.; Ohst, H. Adv. Organomet. Chem. 1986, 25, 199-236.
6. (b) Fu, G. C. Adv. Organomet. Chem. 2001, 47, 101-119.
7. Boese, R.; Finke, N.; Henkelmann, J.; Maier, G.; Paetzold, P.; Reisenauer, H. P.; Schmid, G. Chem. Ber. 1985, 118, 1644-1654. See also: Boese, R.; Finke, N.; Keil, T.; Paetzold, P.; Schmid, G. Z. Naturforsch., B 1985, 40, 1327-1332.
8. Boese, R.; Finke, N.; Henkelmann, J.; Maier, G.; Paetzold, P.; Reisenauer, H. P.; Schmid, G. Chem. Ber. 1985, 118, 1644-1654. See also: Boese, R.; Finke, N.; Keil, T.; Paetzold, P.; Schmid, G. Z. Naturforsch., B 1985, 40, 1327-1332.
9. For some discussions of planar chirality, see: (a) Paley, R. S. Chem. Rev. 2002, 102, 1493-1523.
10. (b) Schlögl, K. Top. Curr. Chem. 1984, 125, 27-62.
11. (c) Cahn, R. S.; Ingold, C.; Prelog, V. Angew Chem., Int. Ed. Engl. 1966, 5, 385-415.
12. 3 fragment serves as a powerful electron-withdrawing substituent (comparable to a nitro group), which should lower the energy of the empty π-symmetry orbitals of the borabenzene and facilitate donation from the filled carbonyl π system: (a) Davies, S. G.; Coote, S. J.; Goodfellow, C. L. Advances in Metal-Organic Chemistry; JAI: Greenwich, CT, 1991; Vol. 2, pp 1-57.
13. (b) Semmelhack, M. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 4, Chapter 2.4.
14. Boese, R.; Finke, N.; Keil, T.; Paetzold, P.; Schmid, G. Z. Naturforsch., B 1985, 40, 1327-1332.
15. Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 1, Chapter 1.10.
16. Bloem, P.; David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1991, 407, C19-C22.
17. 2: Maier, G.; Reisenauer, H. P.; Henkelmann, J.; Kliche, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 295-296.
18. (b) Pyridine- and triethylamine-2-boranaphthalene: ref 6.
19. (c) (Dimethyl sulfide)-9-boraanthracene: Jutzi, P. Angew. Chem., Int. Ed. Engl. 1972, 11, 53-54.
20. Hoic, D. A.; Wolf, J. R.; Davis, W. M.; Fu, G. C. Organometallics 1996, 15, 1315-1318. See also: Tweddell, J.; Hoic, D. A.; Fu, G. C. J. Org. Chem. 1907, 62, 8286-8287. Qiao, S.; Hoic, D. A.; Fu, G. C. Organometallics 1997, 16, 1501-1502.
21. Hoic, D. A.; Wolf, J. R.; Davis, W. M.; Fu, G. C. Organometallics 1996, 15, 1315-1318. See also: Tweddell, J.; Hoic, D. A.; Fu, G. C. J. Org. Chem. 1907, 62, 8286-8287. Qiao, S.; Hoic, D. A.; Fu, G. C. Organometallics 1997, 16, 1501-1502.
22. Hoic, D. A.; Wolf, J. R.; Davis, W. M.; Fu, G. C. Organometallics 1996, 15, 1315-1318. See also: Tweddell, J.; Hoic, D. A.; Fu, G. C. J. Org. Chem. 1907, 62, 8286-8287. Qiao, S.; Hoic, D. A.; Fu, G. C. Organometallics 1997, 16, 1501-1502.
23. Amendola, M. C.; Stockman, K. E.; Hoic, D. A.; Davis, W. M.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 267-269.
24. All other B-O distances for complexes between boron-based Lewis acids and aldehydes fall in the range of 1.49-1.61 Å.
25. 5BPh): Aghe, A. J., III; Shu, P. J. Am. Chem. Soc. 1971, 93, 1804-1805.
26. 5BMe): Herberich, G. E.; Becker, H. J.; Carsten, K.; Engelke, C.; Koch, W. Chem. Ber. 1976, 109, 2382-2388.
27. 2): Herberich G. E.; Schmidt, B.; Englert, U.; Wagner, T. Organometallics 1993, 12, 2891-2893.
28. 2OLi): Herberich, G. E. ; Schmidt, B.; Englert, U. Organometallics 1995, 14, 471-480.
29. 5BNMeBn): Ashe, A. J., III; Kampf, J. W.; Muller, C.; Schneider, M. Organometallics 1996, 15, 387-393.
30. For early applications of boratabenzene-metal complexes in catalysis, see: (a) Bonnemann, H.; Brijoux, W.; Brinkmann, R.; Meurers, W. Helv. Chim. Acta 1984, 67, 1616-1624.
31. (b) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Muller, C. J. Am. Chem. Soc. 1996, 118, 2291-2292.
32. Qiao, S.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1996, 118, 6329-6330.
33. For interesting extensions of this chemistry, see: (a) Putzker, M. A.; Rogers, J. S.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121, 8112-8113.
34. (b) Rogers, J. S.; Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 730-731.
35. For applications of this chemistry to the synthesis of boratabenzene-zirconium complexes that have intriguing activity in Ziegler-Natta polymerizations, see: (a) Rogers, J. S.; Bazan, G. C.; Sperry, C. K. J. Am. Chem. Soc. 1997, 119, 9305-9306.
36. (b) Barnhart, R. W.; Bazan, G. C.; Mourey, T. J. Am. Chem. Soc. 1998, 120, 1082-2083.
37. For a series of reviews on aromaticity, see: Schleyer, P. v. R., Ed. Chem. Rev. 2001, 101 (5).
38. Ashe, A. J., III; Butler, W.; Sandford, H. F. J. Am. Chem. Soc. 1979, 101, 7066-7067.
39. Hoic, D. A.; Davis, W. M.; Fu, G. C. J. Am. Chem. Soc. 1995, 117, 8480-8481.
40. Hoic, D. A.; Davis, W. M.; Fu, G. C. J. Am. Chem. Soc. 1996, 118, 8176-8177. See also: Hoic, D. A.; DiMare, M.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 7155-7156.
41. Hoic, D. A.; Davis, W. M.; Fu, G. C. J. Am. Chem. Soc. 1996, 118, 8176-8177. See also: Hoic, D. A.; DiMare, M.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 7155-7156.
42. For reviews of palladium-catalyzed coupling reactions, see: (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
43. (b) Cross-Coupling Reactions: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Series 219; Springer-Verlag: New York, 2002.
44. (c) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002.
45. For a review of palladium-catalyzed coupling reactions of aryl chlorides, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
46. For a discussion of the role of anionic palladium complexes in coupling reactions, see: Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
47. (a) Suzuki reactions: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387-3388. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
48. (a) Suzuki reactions: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387-3388. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
49. (b) Negishi reactions: Dai, C.; Fu, G. C. J. Am. Chem. Soc., 2001, 123, 2719-2724.
50. (c) Stille reactions: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411-2413. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343-6348.
51. (c) Stille reactions: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411-2413. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343-6348.
52. (d) Heck reactions: Littke, A. F.; Fu, G. C. J. Org. Chem. 1990, 64, 10-11. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
53. (d) Heck reactions: Littke, A. F.; Fu, G. C. J. Org. Chem. 1990, 64, 10-11. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
54. (e) See also: Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
55. For an overview of recent progress by others, see ref 26.
56. (a) Suzuki reactions of primary alkyl halides and tosylates: Netherton, M. R.; Dai, C.; Neuschiitz, K.; Fu, G. C. J. Am. Chem. Soc. 20 Kirchhoff, J. H. ; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.01, 123, 10099-10100. Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910-3912. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662-13663.
57. (a) Suzuki reactions of primary alkyl halides and tosylates: Netherton, M. R.; Dai, C.; Neuschiitz, K.; Fu, G. C. J. Am. Chem. Soc. 20 Kirchhoff, J. H. ; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.01, 123, 10099-10100. Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910-3912. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662-13663.
58. (a) Suzuki reactions of primary alkyl halides and tosylates: Netherton, M. R.; Dai, C.; Neuschiitz, K.; Fu, G. C. J. Am. Chem. Soc. 20 Kirchhoff, J. H. ; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.01, 123, 10099-10100. Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910-3912. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662-13663.
59. (a) Suzuki reactions of primary alkyl halides and tosylates: Netherton, M. R.; Dai, C.; Neuschiitz, K.; Fu, G. C. J. Am. Chem. Soc. 20 Kirchhoff, J. H. ; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.01, 123, 10099-10100. Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910-3912. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662-13663.
60. (b) Stille reactions of primary alkyl halides: Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718-3719. Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079-5082.
61. (b) Stille reactions of primary alkyl halides: Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718-3719. Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079-5082.
62. (c) Hiyama reactions of primary alkyl halides: Lee, J.-Y.; Fu, G. C. J. Am. Chem. Soc. 2003,125, 5616-5617.
63. (d) Zn-Negishi reactions of primary alkyl halides and tosylates: Zhou, J.-R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527-12530.
64. (e) Sonogashira reactions of primary alkyl halides: Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643.
65. (f) Zr-Negishi reactions of primary alkyl halides and tosylates: Wiskur, S. L.; Korte, A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 82-83.
66. (g) Zn-Negishi reactions of secondary alkyl halides: Zhou, J.-R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727.
67. (h) Suzuki reactions of secondary alkyl halides: Zhou, J.-R.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340-1341.
68. In this Perspective, I have chosen to focus on the discoveries that provided the pathway from our interest in chiral Lewis acid chemistry to our program in palladium- and nickel-catalyzed coupling reactions; a comprehensive discussion of the individual projects can be the subject of future reviews.
69. Deng, H.; Jung, J.-K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 9032-9034.
70. Yu, H.-h.; Xu, B.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 1142-1143.