Organic reactions in aqueous media. Cyclopentadienylindium(I) as the first example of organoindium(I) reagent for carbon-carbon bond formation and the demonstration of one-pot tandem addition/intramolecular Diels-Alder reaction in aqueous media

Journal of the American Chemical Society

Volumn 122, Issue 2, 2000, Pages 402-403

  Yang, Yang ^a   Chan, Tak Hang ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HALIDE; INDIUM; ORGANIC COMPOUND;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0343340449     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9928778     Document Type: Article

References (55)

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19. For some recent examples of indium-mediated reactions in aqueous media, see: (a) Paquette, L. A.; Rothhaar, R. R.; Issac, M.; Rogers, L. M.; Rogers, R. D. J. Org. Chem. 1998, 63, 5463. (b) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605. (c) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C. J. J. Org. Chem. 1998, 63, 7472. (d) Loh, T.-P.; Cao, G.-Q.; Pei, J. Tetrahedron Lett. 1998, 39, 1453, 1457.
20. For some recent examples of indium-mediated reactions in aqueous media, see: (a) Paquette, L. A.; Rothhaar, R. R.; Issac, M.; Rogers, L. M.; Rogers, R. D. J. Org. Chem. 1998, 63, 5463. (b) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605. (c) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C. J. J. Org. Chem. 1998, 63, 7472. (d) Loh, T.-P.; Cao, G.-Q.; Pei, J. Tetrahedron Lett. 1998, 39, 1453, 1457.
21. Most investigators have used the sesquihalide formulation to describe the allylindium intermediate in the indium-mediated allylation reactions in organic solvents, see: (a) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538. (b) Bossard, F.; Damabrin, V.; Lintanf, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055. (c) Tussa, L.; Lebreton, C.; Mosset, P. Chem. Eur. J. 1997, 3, 1064. (d) Lloyd- Jones, G. C.; Russell, T. Synlett 1998, 903. (e) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327. (f) Capps, S. M.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Tetrahedron Lett. 1998, 39, 2853.
22. Most investigators have used the sesquihalide formulation to describe the allylindium intermediate in the indium-mediated allylation reactions in organic solvents, see: (a) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538. (b) Bossard, F.; Damabrin, V.; Lintanf, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055. (c) Tussa, L.; Lebreton, C.; Mosset, P. Chem. Eur. J. 1997, 3, 1064. (d) Lloyd- Jones, G. C.; Russell, T. Synlett 1998, 903. (e) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327. (f) Capps, S. M.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Tetrahedron Lett. 1998, 39, 2853.
23. Most investigators have used the sesquihalide formulation to describe the allylindium intermediate in the indium-mediated allylation reactions in organic solvents, see: (a) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538. (b) Bossard, F.; Damabrin, V.; Lintanf, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055. (c) Tussa, L.; Lebreton, C.; Mosset, P. Chem. Eur. J. 1997, 3, 1064. (d) Lloyd- Jones, G. C.; Russell, T. Synlett 1998, 903. (e) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327. (f) Capps, S. M.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Tetrahedron Lett. 1998, 39, 2853.
24. Most investigators have used the sesquihalide formulation to describe the allylindium intermediate in the indium-mediated allylation reactions in organic solvents, see: (a) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538. (b) Bossard, F.; Damabrin, V.; Lintanf, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055. (c) Tussa, L.; Lebreton, C.; Mosset, P. Chem. Eur. J. 1997, 3, 1064. (d) Lloyd-Jones, G. C.; Russell, T. Synlett 1998, 903. (e) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327. (f) Capps, S. M.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Tetrahedron Lett. 1998, 39, 2853.
25. Most investigators have used the sesquihalide formulation to describe the allylindium intermediate in the indium-mediated allylation reactions in organic solvents, see: (a) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538. (b) Bossard, F.; Damabrin, V.; Lintanf, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055. (c) Tussa, L.; Lebreton, C.; Mosset, P. Chem. Eur. J. 1997, 3, 1064. (d) Lloyd- Jones, G. C.; Russell, T. Synlett 1998, 903. (e) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327. (f) Capps, S. M.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Tetrahedron Lett. 1998, 39, 2853.
26. Most investigators have used the sesquihalide formulation to describe the allylindium intermediate in the indium-mediated allylation reactions in organic solvents, see: (a) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538. (b) Bossard, F.; Damabrin, V.; Lintanf, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055. (c) Tussa, L.; Lebreton, C.; Mosset, P. Chem. Eur. J. 1997, 3, 1064. (d) Lloyd- Jones, G. C.; Russell, T. Synlett 1998, 903. (e) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327. (f) Capps, S. M.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Tetrahedron Lett. 1998, 39, 2853.
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29. For recents examples see: (a) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Arake, S. J. Org. Chem. 1999, 64, 172. (b) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1999 39, 6327. (c) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
30. For recents examples see: (a) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Arake, S. J. Org. Chem. 1999, 64, 172. (b) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1999 39, 6327. (c) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
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41. As far as we can determine, the only reported reaction of 1 is its Diels-Alder reaction with maleic anhydride. It is quite possible that the reaction is actually not due to 1 but due to cyclopentadiene released from 1. See: Contreras, J. G.; Tuck, D. G. Inorg. Chem. 1973, 12, 2596.
42. 2O (4:1) with stirring at 0 °C. Freshly made cyclopentadienylindium(I) (1.0 mmol) was added and the mixture was stirred at 0°C for 4 h under the protection of argon. The reaction mixture was extracted directly with diethyl ether (3 × 15 mL) and washed with saturated sodium bicarbonate aqueous solution. After evaporation of the solvent, the purified products were obtained from flash chromatography on silica gel using a mixture of hexane and ethyl acetate (10:1) as eluent.
43. The reaction is to be distingushed from the reaction of cyclopentadiene itself with aldehydes in aqueous basic conditions which gave the corresponding fulvenes. See: (a) Little, W. F.; Koestler, R. C. J. Org. Chem. 1961, 26, 3247 (b) Ziegler, K.; Gellet, H. G.; Martin, H.; Schnider, J. Justus Liebigs Ann. Chem. 1954, 589, 91.
44. The reaction is to be distingushed from the reaction of cyclopentadiene itself with aldehydes in aqueous basic conditions which gave the corresponding fulvenes. See: (a) Little, W. F.; Koestler, R. C. J. Org. Chem. 1961, 26, 3247 (b) Ziegler, K.; Gellet, H. G.; Martin, H.; Schnider, J. Justus Liebigs Ann. Chem. 1954, 589, 91.
45. About hydrogen migration in substituted cyclopentadienes see: (a) McLean, S.; Haynes, P Tetrahedron 1965, 21, 2329. (b) McLean, S.; Haynes, P Tetrahedron 1965, 21, 2343.
46. About hydrogen migration in substituted cyclopentadienes see: (a) McLean, S.; Haynes, P Tetrahedron 1965, 21, 2329. (b) McLean, S.; Haynes, P Tetrahedron 1965, 21, 2343.
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48. Prepared and characterized according to literature procedures. See: Poland, J. S.; Tuck, D. G J. Organomet. Chem. 1972, 42, 307.
49. Unreacted aldehydes were recovered from the reaction mixture. The tris-cyclopentadienylindium(III) could not be recovered, presumably due to its facile hydrolysis under the reaction conditions.
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