Traceless, solid-phase synthesis of biarylmethane structures through Pd- catalyzed release of supported benzylsulfonium salts

Angewandte Chemie - International Edition

Volumn 39, Issue 9, 2000, Pages 1679-1683

  Vanier, Cécile ^a   Lorgé, Franz ^a   Wagner, Alain ^a   Mioskowski, Charles ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Cleavage reactions; Cross coupling; Solid phase synthesis; Sulfides; Synthetic methods

Indexed keywords

BENZYL DERIVATIVE; METHANE; PALLADIUM; SULFONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEALKYLATION; HYDROGEN BOND; REACTION ANALYSIS; SYNTHESIS;

EID: 0034595263     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000502)39:9<1679::AID-ANIE1679>3.0.CO;2-4     Document Type: Article

References (43)

1. For reviews, see a) S. J. Shuttleworth, S. M. Allin, P.K. Sharma, Synthesis 1997, 1217-1239; b) K. Balkenhohl, C. von dem Bussche-Hünnenfield, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 1436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 555-600; d) R. C. D. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 3293-3320; e) G. Jung, Combinatorial Peptide and Nonpeptide Libraries: a Handbook, VCH, Weinheim, 1996.
2. For reviews, see a) S. J. Shuttleworth, S. M. Allin, P.K. Sharma, Synthesis 1997, 1217-1239; b) K. Balkenhohl, C. von dem Bussche-Hünnenfield, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 1436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 555-600; d) R. C. D. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 3293-3320; e) G. Jung, Combinatorial Peptide and Nonpeptide Libraries: a Handbook, VCH, Weinheim, 1996.
3. For reviews, see a) S. J. Shuttleworth, S. M. Allin, P.K. Sharma, Synthesis 1997, 1217-1239; b) K. Balkenhohl, C. von dem Bussche-Hünnenfield, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 1436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 555-600; d) R. C. D. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 3293-3320; e) G. Jung, Combinatorial Peptide and Nonpeptide Libraries: a Handbook, VCH, Weinheim, 1996.
4. For reviews, see a) S. J. Shuttleworth, S. M. Allin, P.K. Sharma, Synthesis 1997, 1217-1239; b) K. Balkenhohl, C. von dem Bussche-Hünnenfield, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 1436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 555-600; d) R. C. D. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 3293-3320; e) G. Jung, Combinatorial Peptide and Nonpeptide Libraries: a Handbook, VCH, Weinheim, 1996.
5. For reviews, see a) S. J. Shuttleworth, S. M. Allin, P.K. Sharma, Synthesis 1997, 1217-1239; b) K. Balkenhohl, C. von dem Bussche-Hünnenfield, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 1436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 555-600; d) R. C. D. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 3293-3320; e) G. Jung, Combinatorial Peptide and Nonpeptide Libraries: a Handbook, VCH, Weinheim, 1996.
6. For reviews, see a) S. J. Shuttleworth, S. M. Allin, P.K. Sharma, Synthesis 1997, 1217-1239; b) K. Balkenhohl, C. von dem Bussche-Hünnenfield, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 1436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 555-600; d) R. C. D. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 3293-3320; e) G. Jung, Combinatorial Peptide and Nonpeptide Libraries: a Handbook, VCH, Weinheim, 1996.
7. a) F. W. Forman, I. Sucholeiki, J. Org. Chem. 1995, 60, 523-528;
8. b) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146;
9. b) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146;
10. c) R. Frenette, R. W. Friesen, Tetrahedron Lett. 1994, 35, 9177-9180.
11. a) L. F. Tietze, A. Steinmetz, Angew. Chem. 1996, 108, 682-683; Angew. Chem. Int. Ed. Engl. 1996, 35, 651-652;
12. a) L. F. Tietze, A. Steinmetz, Angew. Chem. 1996, 108, 682-683; Angew. Chem. Int. Ed. Engl. 1996, 35, 651-652;
13. b) T. Vojkovsky, A. Weichsel, M. Pátek, J. Org. Chem. 1998, 63, 3162-3163;
14. c) J. M. Salvino, M. Mervic, H. J. Mason, T. Kiesow, D. Teager, J. Airey, R. Labaudiniere, J. Org. Chem. 1999, 64, 1823-1830;
15. d) A. S. Hernández, J. C. Hodges. J. Org. Chem. 1997, 62, 3153-3157.
16. a) J. M. Cobb, M. T. Fiorini, C. R. Goddard, M.-E. Theoclitou, C. Ahell, Tetrahedron Lett. 1999, 40, 1045-1048;
17. b) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537;
18. b) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537;
19. c) K. C. Nicolaou, J. Pastor, N. Wissinger, F. Murphy, J. Am. Chem. Soc. 1998, 120, 5132-5133;
20. d) Y. Hau, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706;
21. e) K. A. Newlander, B. Chenera, D. F. Veher, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732;
22. f) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268-272.
23. a) J. C. Nelson, J. K. Young, J. S. Moore, J. Org. Chem. 1996, 61, 8160-8168;
24. b) H. P. Buchstaller, Tetrahedron 1998, 54, 3465-3470;
25. c) K. G. Estep, C. E. Neipp, L. M. S. Stramiello, M. D. Adam, M. P. Allen, S. Robinson, H. J. Roskamp, J. Org. Chem. 1998, 63, 5300-5301;
26. d) S. Bräse, J. Köbberling, D. Enders, R. Lazny, M. Wang, S. Brandtner, Tetrahedron Lett. 1999, 40, 2105-2108;
27. e) S. Bräse, M. Schroen, Angew. Chem. 1999, 111, 1139-1142; Angew. Chem. Int. Ed. 1999, 38, 1071-1073.
28. e) S. Bräse, M. Schroen, Angew. Chem. 1999, 111, 1139-1142; Angew. Chem. Int. Ed. 1999, 38, 1071-1073.
29. a) G. W. Kenner, J. R. McDermott, R. C. Sheppard, J. Chem. Soc. Chem. Commun. 1971, 636-637;
30. b) B. J. Backes, J. A. Ellman, J. Am. Chem. Soc. 1994, 116, 11171-11172;
31. c) B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056.
32. a) A. R. Brown, D. C. Rees, Z. Rankovic, J. R. Murphy, J. Am. Chem. Soc. 1997, 119, 3288-3295;
33. b) C. R. Millington, R. Quarrell, G. Lowe, Tetrahedron Lett. 1998, 39, 7201-7204;
34. c) S. Bräse, D. Enders, J. Kobberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3513-3415.
35. c) S. Bräse, D. Enders, J. Kobberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3513-3415.
36. a) J. Srogl, G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1997, 119, 12376-12377;
37. b) S. Zhang, D. Marshall, L. S. Liebeskind, J. Org. Chem. 1999, 64, 2796-2804.
38. The phenyltetramethylenesulfonium salt was synthesized by the reaction of thiophenol (1 equiv) with 1,4-dibromobutane (2 equiv) in the presence of triethylamine (1.5 equiv) in diethyl ether. The insoluble salt was purified by trituration with ethanol/diethyl ether. All other salts were prepared by alkylation (methylation or ethylation) of the corresponding sulfide. Several alkylating agents were tested. The use of methyl iodide, even in large excess, gave very slow and incomplete reactions. Very good results were obtained with methyl triflate. However, this method was found to be expensive and not practical to carry out. Thus, triethyloxonium tetrafluoroborate was preferred for a quick (1 or 2 h) and quantitative synthesis of sulfonium salts. Purifications of the salts were performed by trituration in ecthanol/diethyl ether.
39. G. A. Crosby, M. Kato, J. Am. Chem. Soc. 1977, 99, 278-280.
40. 2. RT. 15 h; c) thiourea (5 equiv), DMF, 70 C, 17 h; d) benzylamine (3 equiv), toluene, 70 C, 14 h. (matrix presented)
41. Reagents and conditions for the grafting of the substrate on the solid support: 4-cyanobenzylbromide (3 equiv). DIEA (3 equiv), DMF, 70 C, 14 h.
42. E. Lorgé, A. Wagner, C. Mioskowski, J. Comb. Chem. 1999, 1, 25-27.
43. S. Yamagushi, S. Ohno, K. Tamao, Synlett 1997, 1199-1201.