Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates: Development and optimization of a mild and stereospecific coupling process

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2165-2168

  Denmark, Scott E ^a   Regens, Christopher S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANESULFONIC ACID; ALKENYL GROUP; BRONSTED BASE; FLUORINE; NUCLEOPHILE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL BOND; CROSS COUPLING REACTION; STEREOSPECIFICITY;

EID: 79953193707     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.133     Document Type: Article

References (83)

1. (a)Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds., 2nd ed.; Wiley-VCH: Weinheim, 2004;
2. (b) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; University Science Books: Sausalito, 1999;
3. (c)Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley Interscience: New York, 2002;
4. (d)Cross-Coupling Reactions: A Practical Guide; Miyaura, N., Ed. Topics in Current Chemistry; Springer: Berlin, 2002; Vol. 219,.
5. (a) Negishi, E.; Liu, F. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P., Eds.; Wiley, 1998; pp 1-11;
6. (b) Negishi, E. J. Organomet. Chem. 2002, 653, 34-40.
7. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723;
8. (b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411-2413;
9. (c) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561;
10. (d) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028;
11. (e) Navarro, O.; Kelly, R. A., III; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194-16195; For a recent review on the development of ligands for the cross-coupling of aryl chlorides, see:
12. (f) Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283-2321.
13. For organotin coupling to triflates, see: (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486;
14. (b) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033-3040;
15. (c) Kwon, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114-3118; For organoboron coupling to triflates, see:
16. (d) Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208.
17. (a) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060-1065;
18. (b) Percec, V.; Bae, J.-Y.; Zhao, M.; Hill, D. H. J. Org. Chem. 1995, 60, 176-185;
19. (c) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895-6903;
20. (d) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem. 2004, 69, 3447-3452;
21. (e) Naber, J. R.; Fors, B. R.; Wu, X.; Gunn, J. T.; Buchwald, S. L. Heterocycles 2010, 80, 1215-1226;
22. (f) Kuroda, J.; Inamota, K.; Hiroya, K.; Doi, T. Eur. J. Org. Chem. 2009, 2251-2261;
23. (g) So, C. M.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 8059-8063;
24. (h) So, C. M.; Lee, H. W.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2009, 11, 317-320;
25. (i) Zhang, L.; Qing, J.; Yang, P.-Y.; Wu, J. Org. Lett. 2008, 10, 4971-4974;
26. (j) Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531-8534;
27. (k) Ueda, M.; Saitoh, A.; Oh-tani, S.; Miyuara, N. Tetrahedron 1998, 54, 13079-13086.
28. (a) Steinhuebel, D.; Baxter, J. M.; Palucki, M.; Davies, I. W. J. Org. Chem. 2005, 70, 10124-10127;
29. (b) Huffman, M.; Yasuda, N. Synlett 1999, 4, 471-473;
30. (c) Fu, X.; Zhang, S.; Yin, J.; McAllister, T. L.; Jiang, S. A.; Tann, C.; Thiruvengadam, T. K.; Zhang, F. Tetrahedron Lett. 2002, 43, 573-576;
31. (d) Wu, J.; Liao, Y.; Yang, Z. J. Org. Chem. 2001, 66, 3642-3645;
32. (e) Schio, L.; Chatreaux, F.; Klich, M. Tetrahedron Lett. 2000, 41, 1543-1547;
33. (f) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704-8705; (R)-1-[(Sp)-2-(dicyclohexylphosphino)ferrocenyl]ethylditert-butylphosphine (Josi-Phos),
34. (g) Klapars, A.; Campos, K. R.; Chen, C. Y.; Volante, R. P. Org. Lett. 2005, 7, 1185-1188;
35. (h) Zhang, L.; Meng, T.; Jie Wu, J. J. Org. Chem. 2007, 72, 9346-9349;
36. (i) Bhayana, B.; Fors, B. P.; Buchwald, S. L. Org. Lett. 2009, 11, 3954-3957;
37. (j) So, C. M.; Lau, C. P.; Chan, A. S. C.; Kwong, F. Y. J. Org. Chem. 2008, 73, 7731-7734;
38. (k) Wilson, D. A.; Wilson, C. J.; Rosen, B. M.; Percec, V. Org. Lett. 2008, 10, 4879-4882;
39. (l) Zhang, L.; Meng, T.; Wu, J. J. Org. Chem. 2007, 72, 9346-9349;
40. (m) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818-11819;
41. (n) Brenstrum, T.; Gerristma, D. A.; Adjabeng, G. M.; Frampton, C. S.; Britten, J.; Robertson, A. J.; McNulty, J.; Capretta, A. J. Org. Chem. 2004, 69, 7635-7639.
42. (a) Hayashi, T.; Yoshio, K.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449-4452;
43. (b) Gauthier, D.; Beckendorf, S.; Gøgsig, T. M.; Lindhardt, A. T.; Skrydstrup, T. J. Org. Chem. 2009, 74, 3536-3539;
44. (c) Huffman, M. A.; Yasuda, N. Synlett 1998, 471-473;
45. (d) Nan, Y.; Yang, Z. Tetrahedron Lett. 1999, 40, 3321-3324;
46. (e) Lepifre, F.; Buon, C.; Rabot, R.; Bouyssou, P.; Coudert, G. Tetrahedron Lett. 1999, 40, 6373-6376.
47. (a) Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J. Am. Chem. Soc. 2009, 131, 17748-17749;
48. (b) Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422-14423; For reviews, see.;
49. (c) Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2009, 48, 3565-3568;
50. (d) Goossen, L. J.; Goossen, K.; Stanciu, C. Angew. Chem., Int. Ed. 2009, 48, 3569-3571;
51. (e) Knochel, P.; Gavryushin, A. Synfacts 2009, 200;
52. Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 14468-14470.
53. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-523;
54. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1998, 50, 1-652;
55. (c) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. Chapter 4.
56. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483;
57. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. Chapter 2;
58. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
59. (a) Negishi, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley and Sons: New York, 2002; Vol. 1,;
60. (b) Fugami, K; Kosugi, M. Top. Curr. Chem. 2002, 219, 87-130. and references cited therein;
61. (c) Miyaura, N. Top. Curr. Chem. 2002, 219, 11-59. and references cited therein;
62. (d) Hassan, J.; Sevigonon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469;
63. (e) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
64. For the reviews on the synthesis of organo-triflates and nonaflates, see: (a) Stang, P. J.; Hanack, M.; Subrmanian, L. R. Synthesis 1982, 85-126;
65. (b) Ritter, K. Synthesis 1993, 735-762.
66. For reviews, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846;
67. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531-1541;
68. (c) Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 75-85;
69. (d) Denmark, S. E.; Sweis, R. F. In Metal Catalyzed Cross-Coupling Reactions; de Meijere, A., Ed.; Wiley-VCH: Weinheim, 2004. Chapter 4.
70. (a) Denmark, S. E.; Baird, J. D. Chem. Eur. J. 2006, 12, 4954-4963;
71. (b) Denmark, S. E.; Regens, C. S. Acc. Chem. Res. 2008, 41, 1486-1499.
72. Denmark, S. E.; Smith, R. C.; Chang, T. W.-T.; Muhuhi, J. M. J. Am. Chem. Soc. 2009, 131, 3104-3118.
73. (a) Denmark, S. E.; Kallemeyn, J. M. J. Am. Chem. Soc. 2006, 128, 15958-15959;
74. (b) Denmark, S. E.; Baird, J. D. Tetrahedron 2009, 65, 3120-3129.
75. Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1990, 31, 2719-2722.
76. Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771-3774.
77. Neuville, L.; Bigot, A.; Dau, M. E. T. H.; Zhu, J. J. Org. Chem. 1999, 64, 7638-7642.
78. Heptenyldimethylsilanol (E)-1 was prepared according to known methods: Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565-568.
79. It has been reported that nonaflates are less susceptible than triflates to nucleophilic attack at the sulfur atom. We propose that this is the source of the undesired phenol formation. Riggleman, S.; DeShong, P. J. Org. Chem. 2003, 68, 8106-8109.
80. 12. It should also be noted that polar coordinating solvents such as THF, diglyme, dioxane, and dimethoxyethane (DME) facilitated cross-coupling: however, the best results were obtained using dioxane as the solvent.
81. X-Phos was chosen as the ligand because it has been reported to prevent cyclometalation of palladium to the ligand especially in cationic palladium complexes. For recent reviews on dialkylbiaryl phosphine ligands see: (a) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461-1473;
82. (b) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361.
83. Extensive optimization of all reaction variables was conducted ligands (NHC, bidentate, monodendate, etc.), palladium precatalysts, additives and solvents. It was found from these studies that Buchwald type dialkylbiaryl phosphine ligands were optimal in ethereal solvents (THF, dioxane, and DME); while all other combinations surveyed did not significantly improve the product yield. It should also be noted that the major side products observed in these reactions were disiloxane formation, from dimerization of (E)-1, and/or S-O bond cleavage.