New radical allylation reaction of iodides

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7410-7411

  Le Guyader, Frédéric ^a   Quiclet Sire, Béatrice ^a   Seguin, Stéphanie ^a   Zard, Samir Z ^a,b  

^a CNRS   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; PROPRIOCEPTION; REACTION ANALYSIS;

EID: 0030742721     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9708878     Document Type: Article

References (58)

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38. The reverse process, i.e., abstraction of iodine from a sulfonyl iodide, is very efficient: (a) Serra, A. C.; da Silva Corrêa, C. M. M.; Vieira, M. A. M. S. A.; Gomes, M. A. Tetrahedron 1990, 46, 3061-3070. (b) Serra, A. C.; da Silva Corrêa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463-9488 and references cited therein.
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40. (Methyl radicals, generated stoichiometrically by iron-catalyzed decomposition of hydrogen peroxide in dimethyl sulfoxide, have been used to generate alkyl radicals from iodides, see: Fontana, F.; Minisci, F.; Vismara, E. Tetrahedron Lett. 1988, 29, 1975-1978.
41. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
42. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
43. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
44. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
45. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
46. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
47. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
48. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
49. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
50. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
51. Alkyl allyl sulfone can be made to extrude sulfur dioxide under certain conditions to give allylated derivatives: (a) Quiclet-Sire B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209-1210. For other radical reactions involving allyl sulfones, see: (b) Phillips, E. D.; Whitham G. H. Tetrahedron Lett. 1993, 34, 2537-2540; 2541-2544. (c) Smith T. A. K.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1989, 313-317; 319-325. (d) Knight, D. J.; Lin, P.; Whitham, G. H. J Chem. Soc., Perkin Trans. 1 1987 2707-2713. (e) Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298-306. (f) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193-3196; J. Org. Chem. 1990, 55, 955-964. (g) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. J. Org. Chem. 1991, 56, 3556-3564. (h) Barre, V.; Uguen, D. Tetrahedron Lett. 1987, 28, 6045-6048. (i) Baechler, R. D.; Bentley, P.; Deuring, L.; Fisk, S. Tetrahedron Lett. 1982, 23, 2269-2272. (j) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610.
52. A typical experimental procedure is as follows: A solution of iodide 1a-h (1 mmol) and allyl ethyl sulfone 2a-c (3 mmol) in degassed heptane (4 mL) or a 1:1 mixture of heptane and chlorobenzene (4 mL) was heated under reflux in the presence of AIBN (0.1 to 0.2 mmol), added portionwise over the course of the reaction which took 10-25 h as indicated by TLC monitoring. The solvents were evaporated under reduced pressure, and the residue was chromatographed on a silica gel column to afford the desired allyl derivatives 4a-h. In some cases, the purification was greatly simplified by heating the crude residue in an oil bath at 50-60 °C under a stream of dry air (or nitrogen) for a few hours to remove excess allyl ethyl sulfone.
53. (a) Garegg P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1980 2866-2869.
54. (b) Garegg, P. J.; Johansson, R.; Ortega, C.; Samuelsson, B. J Chem. Soc., Perkin Trans. 1 1982, 681-683.
55. The relative stereochemistry, where applicable, was assigned by NMR and especially by comparison of the spectra with those of the starting iodides, whose stereochemistry is defined by the iodolactonization reaction. For 4a and 4c the diastereomers could not be separated by preparative chromatography, in contrast to 4b, 4ć, and 4d. In all cases, the diastereomeric ratio was confirmed by GC/MS. See the Supporting Information for details.
56. Reagents 2a-c are made by substituting the correponding allyl bromide or chloride with ethanethiol followed by oxidation to the sulfone: (a) Svata, V.; Prochazka, M.; Bakos, V. Coll. Czech. Chem. Commun. 1978, 43, 2619-2634 (b) Böhme, H.; Bentler, H. Chem. Ber. 1956, 89, 1464-1468.
57. Reagents 2a-c are made by substituting the correponding allyl bromide or chloride with ethanethiol followed by oxidation to the sulfone: (a) Svata, V.; Prochazka, M.; Bakos, V. Coll. Czech. Chem. Commun. 1978, 43, 2619-2634 (b) Böhme, H.; Bentler, H. Chem. Ber. 1956, 89, 1464-1468.
58. See, for example: Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139.