Two palladium-catalyzed domino reactions from one set of substrates/reagents: Efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered Grignard reagents

Organic Letters

Volumn 9, Issue 2, 2007, Pages 363-366

  Dong, Cheng Guo ^a   Yeung, Pik ^a   Hu, Qiao Sheng ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKYNE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDENE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM; STILBENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETATES; ALKYNES; CATALYSIS; INDENES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM; STILBENES;

EID: 33846580541     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062885a     Document Type: Article

References (60)

1. (a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001-1020.
2. (b) Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967-1983.
3. (c) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551-564.
4. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206.
5. (e) Tietze, L. F. Chem. Rev. 1996, 96, 115-136 and references cited therein.
6. (a) de Meijere, A.; von Zezschwitz, P.; Brase, S. Acc. Chem. Res. 2005, 38, 413-422.
7. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
8. (c) Ikeda, S.-i. Acc. Chem. Res. 2000, 33, 511-519.
9. (d) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473.
10. (e) Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289-9346.
11. (f) Malacria, M. Chem. Rev. 1996, 96, 289-306 and references cited therein.
12. Selected recent examples of Pd-catalyzed tandem/domino reactions: (a) Mariampillai, B.; Alberico, D.; Bidau, V.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 14436-14437.
13. (b) Bertrand, M. B.; Wolfe, J. P. Org. Lett. 2006, 8, 2353-2356.
14. (c) Leclerc, J.-P.; Andre, M.; Fagnou, K. J. Org. Chem. 2006, 71, 1711-1714.
15. (d) Henderson, J. L.; Edwards, A. S.; Greaney, M. F. J. Am. Chem. Soc. 2006, 128, 7426-7427.
16. (e) Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. Org. Lett. 2006, 8, 4927-4930.
17. (f) Martins, A.; Marquardt, U.; Kasravi, N.; Alberico, D.; Lautens, M. J. Org. Chem. 2006, 71, 4937-4942.
18. (g) Hay, M. B.; Wolfe, J. P. J. Am. Chem. Soc. 2005, 127, 16468-16476.
19. (h) Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560-14561.
20. (i) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148-13149.
21. (j) Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 701-704.
22. (k) Ohno, H.; Yamamoto, M.; Iuchi, M.; Tanaka, T. Angew. Chem., Int. Ed. 2005, 44, 5103-5106.
23. (l) Yang, Q.; Ney, J. E.; Wolfe, J. P. Org. Lett. 2005, 7, 2575-2578.
24. (m) Cheung, W. S.; Patch, R. J.; Player, M. R. J. Org. Chem. 2005, 70, 3741-3744.
25. (n) Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 701-704.
26. (o) Ganton, M. D.; Kerr, M. A. Org. Lett. 2005, 7, 4777-4779.
27. (p) Abbiati, G.; Arcadi, A.; Canevari, V.; Capezzuto, L.; Rossi, E. J. Org. Chem. 2005, 70, 6454-6460.
28. (q) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460-7461.
29. (r) Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621.
30. (s) Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605-3608.
31. For examples: (a) Nakhla, J. S.; Kampf, J. W.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 2893-2901.
32. (b) Ney, J. E.; Wolfe, J. P. J. Am. Chem. Soc. 2005, 127, 8644-8651. Also see refs 1 and 2.
33. (a) Dong, C.-G.; Hu, Q.-S. Org. Lett. 2006, 8, 5057-5060.
34. (b) Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289-2292.
35. Recent reviews for carbopalladation of alkynes: (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2310.
36. (b) de Meijere, A.; von Zezschwitz, P.; Brase, S. Acc. Chem. Res. 2005, 38, 413-422.
37. Recent reviews for C-H activation: (a) Dyker, G., Ed. Handbook of C-H Transformations: Application in Organic Synthesis; Wiley-VCH: Weinheim, 2005; Vol. 2.
38. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.
39. (c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
40. (d) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633-639.
41. 3 C-H activation: (a) Baudoin, O.; Herrbach, A.; Gueritte, F. Angew. Chem., Int. Ed. 2003, 42, 5736-5740.
42. (b) Suau, R.; Lopez-Romero, J. M.; Rico, R. D. Tetrahedron Lett. 1996, 37, 9357-9360.
43. (c) Dyker, G. J. Org. Chem. 1993, 58, 6426-6428.
44. (d) Dyker, G. Angew. Chem., Int. Ed. 1994, 33, 103-105.
45. (e) Dyker, G. Angew. Chem., Int. Ed. 1992, 31, 1023-1025.
46. (a) Alt, H. G.; Köppl, A. Chem. Rev. 2000, 100, 1205-1222.
47. (b) Korte, A.; Legros, J.; Bolm, C. Synlett 2004, 13, 2397-2399 and references therein.
48. (c) Barbera, J.; Rakitin, O. A.; Ros, M. B.; Torroba, T. Angew. Chem., Int. Ed. 1998, 37, 296-299.
49. Substituted indenes were typically prepared in more than one step. For recent examples of one-pot access to substituted indenes with different substitution patterns from 2-(2-(1-alkynyl)phenyl)malonates or 2-(2-halophenyl)malonate: (a) Guo, L.-N.; Duan, X.-H.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2006, 71, 3325-3327.
50. (b) Zhang, D.; Yum, E. K.; Liu, Z.; Larock, R. C. Org. Lett. 2005, 7, 4963-4966.
51. Also see: (c) Kuninobu, Y.; Nishina, Y.; Takai, K. Org. Lett. 2006, 8, 2891-2893.
52. (d) Nakamura, I.; Bajracharya, G. B.; Wu, H.; Oishi, K.; Mizushima, Y.; Gridnev, I. D.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 15423-15430.
53. (a) Rathore, R.; Lindeman, S. V.; Kochi, J. K. Angew. Chem. 1998, 110, 1665-1667;
54. Angew. Chem., Int. Ed. 1998, 37, 1585-1587.
55. (b) Irie, M. Chem. Rev. 2000, 100, 1685-1716.
56. The most efficient preparation methods reported so far involve the use of 1,2-dibromoalkenes with hindered Grignard reagents: (a) Rathore, R.; Deselnicu, M. I.; Burns, C. L. J. Am. Chem. Soc. 2002, 124, 14832-14833.
57. For other methods: (b) Maeda, K.; Okamoto, Y.; Morlender, N.; Haddad, N.; Eventova, I.; Biali, S. E.; Rappoport, Z. J. Am. Chem. Soc. 1995, 117, 9686-9689.
58. (c) Bottino, F. A.; Finocchiaro, P.; Libertini, E.; Reale, A.; Recca, A. J. Chem. Soc., Perkin Trans. 2 1982, 77-81.
59. A similar regioselectivity trend was observed in Pd-catalyzed three-component reactions of aryl iodides, internal alkynes, and arylboronic acids: Zhou, C.; Larock, R. C. J. Org. Chem. 2005, 70, 3765-3777.
60. 2-catalyzed reactions of trans-1,2-dibromo-1,2-diphenylethene or trans-3,4-dibromo-3-hexene with 2-mesitylmagnesium bromide or 2,6-dimethylphenylmagnesium bromide in refluxing THF gave significant amounts of substituted indenes (> 18%). When the reaction temperature was 60°C, substituted indenes were obtained in 70-98% yields.