Synthesis of 2-naphthols via carbonylative stille coupling reaction of 2-bromobenzyl bromides with tributylallylstannane followed by the heck reaction

Journal of Organic Chemistry

Volumn 76, Issue 24, 2011, Pages 10068-10077

  Dai, Yao ^a   Feng, Xiujuan ^a   Liu, Hesong ^b   Jiang, Hua ^a   Bao, Ming ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b THE FIRST HOSPITAL OF JILIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2-NAPHTHOLS; BASIC CONDITIONS; GOOD YIELD; HECK REACTIONS; STILLE COUPLING REACTION; UNSATURATED KETONES;

BROMINE COMPOUNDS; KETONES; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

1 (1 BROMONAPHTHALEN 2YL)PENT 3 EN 2 ONE; 1 (2 BROMO 4 CHLOROPHENYL)PENT 3 EN 2 ONE; 1 (2 BROMO 4 FLUOROPHENYL)PENT 3 EN 2 ONE; 1 (2 BROMO 4 METHYLPHENYL)PENT 3 EN 2 ONE; 1 (2 BROMO 4,5 DIMETHOXYPHENYL)PENT 3 EN 2 ONE; 1 (2 BROMOPHENYL)PENT 3 EN 2 ONE; 1 (2 CHLOROPHENYL)PENT 3 EN 2 ONE; 1 (2 ROMOPHENYL)PENT 3 EN 2 ONE; 1 (2,4 DIBROMOPHENYL)PENT 3 EN 2 ONE; 2 NAPHTHOL; 4 METHYL 3,4 DIHYDRONAPHTHALEN 2 ONE; 4 METHYLNAPHTHALEN 2 OL; 6 CHLORO 4 METHYLNAPHTHALEN 2 OL; 6 FLUORO 4 METHYLNAPHTHALEN 2 OL; 6 METHOXY 4 METHYLNAPHTHALEN 2 OL; 6,7 DIMETHOXY 4 METHYLNAPHTHALEN 2 OL; BROMINE DERIVATIVE; BROMOBENZYL BROMIDE; CARBON MONOXIDE; CHEMICAL AGENT; TRIBUTYLALLYLSTANNANE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATIVE STILLE COUPLING REACTION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HECK REACTION; ISOMERIZATION; ONE POT SYNTHESIS; REACTION OPTIMIZATION;

BIOLOGICAL AGENTS; CARBON MONOXIDE; CATALYSIS; ISOMERISM; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NAPHTHOLS; TIN COMPOUNDS;

EID: 84055193843     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201907t     Document Type: Article

References (51)

1. (a) Wang, H. Chirality 2010, 22, 827.
2. (b) Gorth, F. C.; Rucker, M.; Eckhardt, M.; Bruckner, R. Eur. J. Org. Chem. 2000, 2605.
3. (c) Krohn, K.; Zimmermann, G. J. Org. Chem. 1998, 63, 4140.
4. (d) Zhao, H.; Neamati, N.; Mazumder, A.; Sunder, S.; Pommier, Y.; Burke, T. R. J. Med. Chem. 1997, 40, 1186.
5. see: (a) Juteau, H.; Gareau, Y.; Lachance, H. Tetrahedron Lett. 2005, 46, 4547.
6. (b) Zhang, X. X.; Sarkar, S.; Larock, R. C. J. Org. Chem. 2006, 71, 236.
7. see: (a) Kel'in, A. V.; Kozyrkov, Y. Y. Synthesis 1998, 729.
8. (b) Daniewski, A. R.; Kiegiel, J. J. Org. Chem. 1988, 53, 5535.
9. (c) Teresa, J. D.; Mateos, A. F.; Gonzalez, R. R. Tetrahedron Lett. 1982, 23, 3405.
10. see: (a) Cooke, H. A.; Zhang, J.; Griffin, M. A.; Nonaka, K.; Van Lanen, S. G.; Shen, B.; Bruner, S. D. J. Am. Chem. Soc. 2007, 129, 7728.
11. (b) Ji, N.; Rosen, B. M.; Myers, A. G. Org. Lett. 2004, 6, 4551.
12. (c) Citterio, A.; Pesce, L.; Sebastiano, R.; Santi, R. Synthesis 1990, 142.
13. see: (a) Collomb, D.; Chantegrel, B.; Deshayes, C. Tetrahedron 1996, 52, 10455.
14. (b) Taylor, E. C.; Davies, H. M. L. Tetrahedron Lett. 1983, 24, 5453.
15. (a) Padwa, A.; Chiacchio, U.; Fairfax, D. J.; Kassir, J. M.; Litrico, A.; Semones, M. A.; Xu, S. L. J. Org. Chem. 1993, 58, 6429.
16. (b) Padwa, A.; Austin, D. J.; Chiacchio, U.; Kassir, J. M.; Rescifina, A.; Xu, S. L. Tetrahedron Lett. 1991, 32, 5923.
17. see: (a) Fernandez, M. Synthesis 2009, 3051.
18. (b) Martínez, A.; Fernandez, M.; Estevez, J. C.; Estevez, R. J.; Castedo, L. Tetrahedron 2005, 61, 1353 and references cited therein.
19. (c) Martínez, A.; Fernandez, M.; Estevez, J. C.; Estevez, R. J.; Castedo, L. Tetrahedron 2005, 61, 485.
20. see: (a) Fei, Z. B.; McDonald, F. E. Org. Lett. 2005, 7, 3617.
21. (b) Martinez, A. D.; Deville, J. P.; Stevens, J. L.; Behar, V. J. Org. Chem. 2004, 69, 991 and references cited therein.
22. (c) Deville, J. P.; Behar, V. Org. Lett. 2002, 4, 1403.
23. (d) Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2000, 56, 1315.
24. (e) Watanabe, M.; Date, M.; Furukawa, S. Chem. Pharm. Bull. 1989, 37, 292.
25. Tsukamoto, H.; Kondo, Y. Org. Lett. 2007, 9, 4227.
26. (a) Peng, B.; Feng, X. J.; Zhang, X.; Zhang, S.; Bao, M. J. Org. Chem. 2010, 75, 2619.
27. (b) Peng, B.; Feng, X. J.; Zhang, X.; Ji, L. Y.; Bao, M. Tetrahedron 2010, 66, 6013.
28. (c) Lu, S. R.; Xu, Z. W.; Bao, M.; Yamamoto, Y. Angew. Chem., Int. Ed. 2008, 47, 4366.
29. (d) Bao, M.; Nakamura, H.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 759.
30. see: (a) Foster, C. E.; Mackie, P. R. Ketones: α,β-Unsaturated Ketones. In Comprehensive Organic Functional Group Transformations II; Katritzky, A R., Taylor, R J. K, Eds.; Elsevier: Oxford, 2004; Vol. 3, pp 215-266.
31. (b) Ebenezer, W. J.; Wight, P. Ketones: α,β-Unsaturated Ketones. In Comprehensive Organic Functional Group Transformations; Katritzky, A R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 3, pp 205-276.
32. see: (a) Randell-Sly, H. E.; Osborne, J. D.; Woodward, R L.; Currie, G. S.; Willis, M. C. Tetrahedron 2009, 65, 5110 and references cited therein.
33. (b) Wang, S. H.; Tu, Y. Q.; Wang, M. Tetrahedron Lett. 2006, 47, 8621 and references cited therein.
34. (c) Liu, Y. J.; Zhang, Y. M. Tetrahedron Lett. 2004, 45, 1295 and references cited therein.
35. (a) Satyanarayana, G.; Maier, M. E. Org. Lett. 2008, 10, 2361.
36. (b) Bruyère, D.; Gaignard, G; Bouyssi, D.; Balme, G; Lancelin, J.-M. Tetrahedron Lett. 1997, 38, 827.
37. Minatti, A; Zheng, X. L.; Buchwald, S. L. J. Org. Chem. 2007, 72, 9253 and references cited therein.
38. see: Tadd, A. C.; Fielding, M. R; Willis, M. C. Chem. Commun. 2009, 6744.
39. Carpino, L. A; Lin, Y. Z. J. Org. Chem. 1990, 55, 247.
40. Landais, Y.; Robin, J. P.; Lebrun, A. Tetrahedron 1991, 47, 3787.
41. Musso, D. L.; Orr, G. F.; Cochran, F. R; Kelley, J. L.; Selph, J. L.; Rigdon, G C.; Cooper, B. R; Jones, M. L. J. Med. Chem. 2003, 46, 409.
42. Campiani, G; Butini, S.; Fattorusso, C.; Trotta, F.; Gemma, S.; Catalanotti, B.; Nacci, V; Fiorini, I.; Cagnotto, A.; Mereghetti, I.; Mennini, T.; Minetti, P.; Di Cesare, M. A.; Stasi, M. A.; Di Serio, S.; Ghirardi, O.; Tinti, O.; Carminati, P. J. Med. Chem. 2005, 48, 1705.
43. Zhidkov, M. E.; Baranova, O. V; Balaneva, N. N.; Fedorov, S. N.; Radchenko, O. S.; Dubovitskii, S. V Tetrahedron Lett. 2007, 48, 7998.
44. Jolad, S. D.; Rajagopalan, S. Org. Synth. 1966, 46, 13.
45. Chaumontet, M.; Piccardi, R; Audic, N.; Hitce, J.; Peglion, J. L.; Clot, E.; Baudoin, O. J. Am. Chem. Soc. 2008, 130, 15157.
46. Wagner, P. J.; Wang, L. L. Org. Lett. 2006, 8, 645.
47. Bower, J. F.; Szeto, P.; Gallagher, T. Org. Biomol. Chem. 2007, 5, 143.
48. Baxter, G J.; Brown, R F. C. Aust. J. Chem. 1975, 28, 1551.
49. Nagao, Y.; Lee, W. S.; Komaki, Y.; Sano, S.; Shiro, M. Chem. Lett. 1994, 23, 597.
50. Silveira, C. C.; Machado, A.; Braga, A L.; Lenardao, E. J. Tetrahedron Lett. 2004, 45, 4077.
51. Molander, G A.; Cavalcanti, L. N. J. Org. Chem. 2010, 76, 623.