2-(trimethylsilyl)ethyl sulfoxides as a convenient source of sulfenate anions

Synthesis

Volumn , Issue 9, 2007, Pages 1315-1324

  Foucoin, Florian ^a   Caupène, Caroline ^a   Lohier, Jean François ^a   Santos, Jana Sopkova De Oliveira ^a,b   Perrio, Stéphane ^a   Metzner, Patrick ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

Author keywords

Alkylation; Fluorine; Silicon; Sulfenate salts; Sulfoxides

Indexed keywords

ALKYL HALIDES; SULFENATE SALTS; SULFOXIDES;

ALKYLATION; FLUORINE; REACTION KINETICS; SILICON; SULFUR COMPOUNDS;

NEGATIVE IONS;

2 (TRIMETHYLSILYL)ETHYL SULFOXIDE DERIVATIVE; FLUORIDE; HALIDE; SILICON; SULFENATE SALT; SULFOXIDE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 34249017980     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-966017     Document Type: Article

References (73)

1. For a recent review: O'Donnell, J. S.; Schwan, A. L. J. Sulfur Chem. 2004, 25, 183.
2. (a) Forman, H. J.; Fukuto, J. M.; Torres, M. Am. J. Physiol. Cell. Physiol. 2004, 287, C246.
3. (b) Nagahara, N.; Katayama, A. J. Biol. Chem. 2005, 280, 34569.
4. (a) Sandrinelli, F.; Perrio, S.; Beslin, P. J. Org. Chem. 1997, 62, 8626.
5. (b) Sandrinelli, F.; Perrio, S.; Averbuch-Pouchot, M.-T. Org. Lett. 2002, 4, 3619.
6. (c) Sandrinelli, F.; Fontaine, G.; Perrio, S.; Beslin, P. J. Org. Chem. 2004, 69, 6916.
7. (d) Sandrinelli, F.; Boudou, C.; Caupène, C.; Averbuch-Pouchot, M.-T.; Perrio, S.; Metzner, P. Synlett 2006, 3289.
8. (a) Maezaki, N.; Yagi, S.; Ohsawa, S.; Ohishi, H.; Tanaka, T. Tetrahedron 2003, 59, 9895.
9. (b) Maezaki, N.; Yagi, S.; Yoshigami, R.; Maeda, J.; Suzuki, T.; Ohsawa, S.; Tsukamoto, K.; Tanaka, T. J. Org. Chem. 2003, 68, 5550.
10. (c) Maezaki, N.; Yagi, S.; Maeda, J.; Yoshigami, R.; Tanaka, T. Heterocycles 2004, 62, 263.
11. O'Donnell, J. S.; Schwan, A. L. Tetrahedron Lett. 2003, 44, 6293.
12. (a) Caupène, C.; Boudou, C.; Perrio, S.; Metzner, P. J. Org. Chem. 2005, 70, 2812.
13. (b) Maitro, G.; Prestat, G.; Madec, D.; Poli, G. J. Org. Chem. 2006, 71, 7449.
14. (c) Maitro, G.; Vogel, S.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2006, 8, 5951.
15. (a) Oida, T.; Ohnishi, A.; Shimamaki, T.; Hayashi, Y.; Tanimoto, S. Bull. Chem. Soc. Jpn. 1991, 64, 702.
16. (b) Oida, T.; Nakamura, M.; Takashima, Y.; Hayashi, Y. Bull. Inst. Chem. Res., Kyoto Univ. 1992, 70, 295.
17. Benzenesulfenic acid 2-(trimethylsilyl)ethyl ester was prepared by reaction of benzenesulfenyl chloride with 2-(trimethylsilyl)ethyl alcohol. By comparison, the analogous sulfoxides are readily available from commercial compounds according to: (a) Schwan, A. L.; Pippert, M. F. Tetrahedron: Asymmetry 1995, 6, 131.
18. (b) Schwan, A. L.; Brillon, D.; Dufault, R. Can. J. Chem. 1994, 72, 325.
19. The reactivity of more sophisticated β-silyl sulfoxides with TBAF has previously been investigated by the group of Toru, but their attention was focused on the alkene product: (a) Nakamura, S.; Watanabe, Y.; Toru, T. J. Chem. Soc., Perkin Trans. 1 1999, 3403.
20. (b) Nakamura, S.; Takemoto, H.; Ueno, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 469.
21. (c) Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381.
22. (d) Nakamura, S.; Kusuda, S.; Kawamura, K.; Toru, T. J. Org. Chem. 2002, 67, 640.
23. (e) Nakamura, S.; Nakayama, J.-i.; Toru, T. J. Org. Chem. 2003, 68, 5766.
24. Schwan also described a fluoride free deprotection of simple 2-(trimethylsilyl)ethyl sulfoxides by treatment with thionyl chloride to afford sulfinyl chlorides: (f) Schwan, A. L.; Strickler, R. R.; Dunn-Dufault, R.; Brillon, D. Eur. J. Org. Chem. 2001, 1643.
25. (a) Huttunen, K. M.; Kumpalainen, H.; Leppänen, J.; Rautio, J.; Järvinen, T.; Vepsäläinen, J. Synlett 2006, 701.
26. (b) Fustero, S.; García Sancho, A.; Chiva, G.; Sanz-Cervera, J. F.; del Pozo, C.; Aceña, J. L. J. Org. Chem. 2006, 71, 3299.
27. (c) Grecian, S. A.; Hadida, S.; Warren, S. D. Tetrahedron Lett. 2005, 46, 4683.
28. (d) Bottaro, J. C.; Penwell, P. E.; Schmitt, R. J. J. Am. Chem. Soc. 1997, 119, 9405.
29. (e) Varaprasad, C. V. N. S.; Johnson, F. Tetrahedron Lett. 2005, 46, 2163.
30. (f) Thakkalapally, A.; Benin, V. Tetrahedron 2005, 61, 4939.
31. For a review concerning the 2-(trimethylsilyl)ethyl group in synthesis, see: (a) Chambert, S.; Désiré, J.; Décout, J.-L. Synthesis 2002, 2319.
32. See also for deprotection of sulfides: (b) Flatt, A. K.; Dirk, S. M.; Henderson, J. C.; Shen, D. E.; Su, J.; Reed, M. A.; Tour, J. M. Tetrahedron 2003, 59, 8555.
33. (c) Chatterji, T.; Kizil, M.; Keerthi, K.; Chowdhury, G.; Pospisil, T.; Gates, K. S. J. Am. Chem. Soc. 2003, 125, 4996.
34. (d) Hamm, M. L.; Cholera, R.; Hoey, C. L.; Gill, T. J. Org. Lett. 2004, 6, 3817.
35. (e) Pollack, S. K.; Naciri, J.; Mastrangelo, J.; Patterson, C. H.; Torres, J.; Moore, M.; Shashidhar, R.; Kushmerick, J. G. Langmuir 2004, 20, 1838.
36. (f) Morales, G. M.; Jiang, P.; Yuan, S.; Lee, Y.; Sanchez, A.; You, W.; Yu, L. J. Am. Chem. Soc. 2005, 127, 10456.
37. For deprotection of sulfones: (g) Lai, M.-t.; Oh, E.; Shih, Y.; Liu, H.-w. J. Org. Chem. 1992, 57, 2471.
38. (h) Palmer, J. T.; Fuchs, P. L. Synth. Commun. 1988, 18, 233.
39. For deprotection of selenothioic acid S-esters: (i) Murai, T.; Kamoto, T.; Kato, S. J. Am. Chem. Soc. 2000, 122, 9850.
40. (j) Niyomura, O.; Sakai, K.; Murai, T.; Kato, S.; Yamaguchi, S.; Tamao, K. Chem. Lett. 2001, 968.
41. (k) Kimura, T.; Murai, T.; Miwa, A.; Kurachi, D.; Yoshikawa, H.; Kato, S.J. Org. Chem. 2005, 70, 5611.
42. For deprotection of phosphinoselenothioic acid S-esters: (l) Kimura, T.; Murai, T. Chem. Commun. 2005, 4077.
43. (a) Bernhard, W.; Fleming, I. J. Organomet. Chem. 1984, 271, 281.
44. (b) Jones, S. L.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1988, 1153.
45. Wagner, M.; Kunz, H. Synlett 2000, 400.
46. (a) Gornowicz, G. A.; Ryan, J. W.; Speier, J. L. J. Org. Chem. 1968, 33, 2918.
47. (b) Mahadevan, A.; Li, C.; Fuchs, P. L. Synth. Commun. 1994, 24, 3099.
48. (c) Menichetti, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1996, 1511.
49. (a) Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18.
50. (b) Ravikumar, K. S.; Kesavan, V.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Org. Synth., Vol. 80; John Wiley & Sons: London, 2003, 184.
51. 3N.
52. -1, see for example: Fortis, F.; Barbe, B.; Pétraud, M.; Picard, J.-P. Chem. Commun. 1999, 527.
53. 8.
54. -1, R = 0.0386, wR = 0.0997. Selected bond lengths (Å) and angles(deg): Br1-C1 1.8912 (14), S1-O1 1.4930 (13), S1-C4 1.7924 (13), S1-C7 1.8248 (14), Si1-C8 1.8792 (14), Si1-C9 1.8512 (18), Si1-C10 1.862 (2), Si1-C11 1.862 (2), C7-C8 1.512 (2), O1-S1-C4 106.27 (7), O1-S1-C7 106.60 (7), C4-S1-C7 97.78 (6), C11-Si1-C8 106.90 (8), C9-Si1-C8 109.56 (9), C10-Si1-C8 110.30 (10). Program(s)used to solve structure: SHELXS97. Program(s)used to refine structure: SHELXL97. Software used to prepare material for publication: SHELXL97. Crystallographic data for compound lb have been deposited at the Cambridge Crystallographic Data Centre, CCDC No 629340. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK; +44 (1223)336408; E-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk.
55. An intramolecular coordination between the oxygen atom of the sulfoxide group and the silicon center was previously detected at low temperature with the analogous electron deficient trifluorosilyl derivatives: Pestunovich, V. A.; Larin, M. F.; Sorokin, M. S.; Albanov, A. I.; Voronkov, M. G. J. Organomet. Chem. 1985, 280, C17.
56. Similar structural effects involving the 2-(trimethylsilyl)ethyl system have already been mentioned with carboxylate and sulfenate esters: Green, A. J.; Issa, W.; White, J. M. Aust. J. Chem. 1997, 50, 927.
57. See for example: Akazome, M.; Noguchi, M.; Tanaka, O.; Sumikawa, A.; Uchida, T.; Ogura, K. Tetrahedron 1997, 53, 8315.
58. (a) Hogg, D. R.; Robertson, A. J. Chem. Soc., Perkin Trans. 1 1979, 1125.
59. (b) Kobayashi, M.; Toriyabe, K. Sulfur Lett. 1985, 3, 117.
60. 6a
61. Touaibia, M.; Desjardins, M.-A.; Provençal, A.; Audet, D.; Médard, C.; Morin, M.; Breau, L. Synthesis 2004, 2283.
62. (a) Lipshutz, B. M.; Pegram, J. J. Tetrahedron Lett. 1980, 21, 3343.
63. (b) Edwards, M. P.; Doherty, A. M.; Ley, S. V.; Organ, H. M. Tetrahedron 1986, 42, 3723.
64. The reaction was carried out with a mixture of both Z- and E-isomers but also the geometrically pure substrates.
65. A similar reluctance towards fluoridolysis was also observed with the analogous isopropyl derivative and also in the sulfide series: (a) Anderson, M. B.; Ranasinghe, M. G.; Palmer, J. T.; Fuchs, P. L. J. Org. Chem. 1988, 53, 3125.
66. (b) Grundberg, H.; Andergran, M.; Nilsson, U. J. Tetrahedron Lett. 1999, 40, 1811.
67. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879.
68. Yu, C. J.; Chong, Y.; Kayyem, J. F.; Gozin, M. J. Org. Chem. 1999, 64, 2070.
69. Kim, Y. H.; Yoon, C. D. Synth. Commun. 1989, 19, 1569.
70. Seago, A.; Houghton, J.; McCague, R.; Foster, A. B.; Coe, P. L.; Falshaw, A. Biochem. Pharmacol. 1987, 36, 400.
71. Guo, Y.; Darmanyan, A. P.; Jenks, W. S. Tetrahedron Lett. 1997, 38, 8619.
72. Shaw, E.; Bernstein, J.; Losee, K.; Lott, W. A. J. Am. Chem. Soc. 1950, 72, 4362.
73. Schwan, A. L.; Lear, Y. Sulfur Lett. 2000, 23, 111.