Highly regioselective internal heck arylation of hydroxyalkyl vinyl ethers by aryl halides in water

Journal of Organic Chemistry

Volumn 72, Issue 17, 2007, Pages 6390-6396

  Arvela, Riina K ^a   Pasquini, Serena ^b   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE GLYCOL; HALIDE MINERALS; HYDROLYSIS; IONIC LIQUIDS; MICROWAVE IRRADIATION; TOLUENE; WATER;

ELECTRON RICH OLEFINS; ETHYLENE GLYCOL VINYL ETHERS; HECK ARYLATION;

ETHERS;

ACETOPHENONE; ALKENE DERIVATIVE; BROMIDE; ETHYLENE GLYCOL; HALIDE; HYDROXYL GROUP; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENE; VINYL DERIVATIVE; WATER;

ARTICLE; ARYLATION; CATALYSIS; HECK REACTION; HYDROLYSIS; MICROWAVE IRRADIATION; STEREOCHEMISTRY;

HALOGENS; VINYL COMPOUNDS; WATER;

EID: 34547941282     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0705768     Document Type: Article

References (68)

1. Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
2. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
3. Larhed, M.; Hallberg, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, p 1133.
4. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
5. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
6. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.
7. von Schenck, H.; Åkermark, B.; Svensson, M. J. Am. Chem. Soc. 2003, 125, 3503.
8. Deeth, R. J.; Smith, A.; Brown, J. M. J. Am. Chem. Soc. 2004, 126, 7144.
9. Andappan, M. M. S.; Nilsson, P.; von Schenck, H.; Larhed, M. J. Org. Chem. 2004, 69, 5212.
10. Andersson, C. M.; Hallberg, A. J. Org. Chem. 1989, 54, 1502.
11. Andersson, C. M.; Larsson, J.; Hallberg, A. J. Org. Chem. 1990, 55, 5757.
12. Badone, D.; Guzzi, U. Tetrahedron Lett. 1993, 34, 3603.
13. Stadler, A.; von Schenck, H.; Vallin, K. S. A.; Larhed, M.; Hallberg, A. Adv. Synth. Catal. 2004, 346, 1773.
14. Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
15. Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558.
16. Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481.
17. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
18. For a recent mechanistic study on internal Heck arylation of electron-rich olefins, see: Amatore, C.; Godin, B.; Jutand, A.; Lemaître, F. Organometallics 2007, 26, 1757.
19. For computational DFT calculations about α/β-selectivity under neutral conditions, see: Datta, G. K.; von Schenk, H.; Hallberg, A.; Larhed, M. J. Org. Chem. 2006, 71, 3896.
20. For a few recent examples, see: (a) Arefalk, A.; Larhed, M.; Hallberg, A. J. Org. Chem. 2005, 70, 938.
21. (b) Hansen, A. L.; Skrydstrup, T. J. Org. Chem. 2005, 70, 5997.
22. (c) Hansen, A. L.; Skrydstrup, T. Org. Lett. 2005, 7, 5585.
23. (d) Vallin, K. S. A.; Zhang, Q.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 2003, 68, 6639.
24. (e) Tu, T.; Hou, X.-L.; Dai, L.-X. Org. Lett. 2003, 5, 3651.
25. Vallin, K. S. A.; Larhed, M.; Hallberg, A. J. Org. Chem. 2001, 66, 4340.
26. Xu, L. J.; Chen, W. P.; Ross, J.; Xiao, J. L. Org. Lett. 2001, 3, 295.
27. Vallin, K. S. A.; Emilsson, P.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6243.
28. Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751.
29. Pei, W.; Mo, J.; Xiao, J. L. J. Organomet. Chem. 2005, 690, 3546.
30. Hyder, Z.; Mo, J.; Xiao, J. L. Adv. Synth. Catal. 2006, 348, 1699.
31. Mo, J.; Xu, L. J.; Ruan, J. W.; Liu, S. F.; Xiao, J. L. Chem. Commun. 2006, 3591.
32. Mo, J.; Liu, S. F.; Xiao, J. L. Tetrahedron 2005, 61, 9902.
33. Amatore, C.; Godin, B.; Jutand, A.; Lemaître, F. Chem. - Eur. J. 2007, 13, 2002.
34. Sheldon, R. A. Green Chem. 2005, 7, 267.
35. For a few recent reviews about the use of aqueous media in carbon-carbon bond formations, see: (a) Li, C.-J. Chem. Rev. 2005, 105, 3095.
36. (b) Beletskaya, I. P.; Cheprakov, A. V. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 2, p 2957.
37. (c) Genet, J. P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305.
38. For a few general reviews, see: (a) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.
39. (b) Leadbeater, N. E. Chem. Commun. 2005, 23, 2881.
40. (c) Grieco, P. A. Organic Synthesis in Water, 1st ed.; Blackie Academic & Professional: London, 1998.
41. For a few recent examples, see: (a) Arefalk, A.; Wannberg, J.; Larhed, M.; Hallberg, A. J. Org. Chem. 2006, 71, 1265.
42. (b) References 20a,d.
43. (c) Bengtson, A.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 5854.
44. High-quality ultrapure Millipore water was used in all reactions. However, regular tap water provides identical reaction outcome according to GC/MS analysis.
45. 1H NMR integral of the methoxy group of 5a was compared to integrals of a known amount of 2,3-dimethylnaphthalene used as an internal standard.
46. 3 (Method B), reactions with 2a appear to be homogeneous, not biphasic, at 90°C.
47. Difficulties in using 4-nitrophenyl substrates have been previously reported; see ref 33c.
48. Mo, J.; Xiao, J. Angew. Chem., Int. Ed. 2006, 45, 4152.
49. For a few examples, see: (a) Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742.
50. (b) Ben-David, Y.; Gozin, M.; Portnoy, M.; Milstein, D. J. Mol. Catal. 1992, 73, 173.
51. (c) Ben-David, Y.; Portnoy, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1989, 1816.
52. (d) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665.
53. Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
54. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
55. Portnoy, M.; Ben-David, Y.; Milstein, D. Organometallics 1993, 12, 4734.
56. Portnoy, M.; Ben-David, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465.
57. Noncyclic, N-alkylated enamides have been reported to undergo unselective arylation in water - DMF mixtures; see ref 21.
58. For a few examples, see: (a) Kondolff, I.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2006, 765.
59. (b) Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Angew. Chem., Int. Ed. 2005, 44, 149.
60. (c) Kondolff, I.; Doucet, H.; Santelli, M. Synlett 2004, 1561.
61. (d) Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J. J. Org. Chem. 1996, 61, 2604.
62. (e) Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287.
63. (f) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133.
64. (g) Bernocchi, E.; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1992, 33, 3073.
65. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488.
66. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
67. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217.
68. Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1991, 113, 2520.