Palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehyde to access 3-aryl- and alkenylphthalides

Journal of Organic Chemistry

Volumn 75, Issue 17, 2010, Pages 6043-6045

  Ye, Zhishi ^a   Qian, Pengcheng ^a   Lv, Guanglei ^a   Luo, Fang ^a   Cheng, Jiang ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLBORONIC ACIDS; INTRAMOLECULAR LACTONIZATION; LACTONIZATION; PHTHALALDEHYDE; PHTHALIDES; TRIFLUOROMETHYL GROUP;

CATALYSIS; FUNCTIONAL GROUPS;

PALLADIUM;

BORONIC ACID DERIVATIVE; PALLADIUM; PHTHALALDEHYDE; PHTHALIDE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; ESTERIFICATION; LACTONIZATION; SUBSTITUTION REACTION; SYNTHESIS;

BENZOFURANS; BORONIC ACIDS; CATALYSIS; CYCLIZATION; LACTONES; MOLECULAR STRUCTURE; O-PHTHALALDEHYDE; PALLADIUM; STEREOISOMERISM;

EID: 77956156644     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101203b     Document Type: Article

References (48)

1. Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1975; Vol. 1, pp 249 - 264.
2. Bellasio, E. German Patent 2422 193, 1974
3. Chem. Abstr. 1975, 83, 9788j.
4. Lacova, M. Chem. Zvesti. 1973, 27, 525
5. Chem. Abstr. 1974, 80, 59757.
6. Elderfield, R. C. Heterocyclic Compounds; Wiley: New York, 1951; Vol. 2, Chapter 2.
7. Aoki, T.; Furusho, T.; Kimura, T.; Satake, S.; Funayama, S. Japanese Patent 7324724, 1973
8. Chem. Abstr. 1974, 80, 129246.
9. Uemura, M.; Take, K.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1983, 858
10. Fei, Z.; McDonald, F. E. Org. Lett. 2007, 9, 3547
11. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378
12. Katsuura, K.; Snieckus, V. Tetrahedron Lett. 1985, 26, 9
13. Patil, M. L.; Borate, H. B.; Ponde, D. E.; Bhawal, B. M.; Deshpande, V. H. Tetrahedron Lett. 1999, 40, 4437
14. Gonnot, V.; Tisserand, S.; Nicolas, M.; Baati, R.; Mioskowski, C. Tetrahedron Lett. 2007, 48, 7117
15. Patil, M. L.; Borate, H. B.; Ponde, D. E.; Deshpande, V. H. Tetrahedron 2002, 58, 6615
16. Sartori, G.; Bigi, F.; Tao, X.; Porta, C.; Maggi, R.; Predieri, G.; Lanfranchi, M.; Pellinghelli, M. A. J. Org. Chem. 1995, 60, 6588
17. Knepper, K.; Ziegert, R. E.; Brase, S. T. Tetrahedron 2004, 60, 8591 and references therein.
18. Cho, C. S.; Baek, D. Y.; Kim, H. Y.; Shim, S. C.; Oh, D. H. Synth. Commun. 2000, 30, 1139
19. Hung, T. V.; Mooney, B. A.; Prager, R. H.; Tippett, J. M. Aust. J. Chem. 1981, 34, 383
20. Chiusoli, G. P.; Salerno, G. Adv. Organomet. Chem. 1979, 17, 195
21. Yang, X.; Rotter, T.; Piazza, C.; Knochel, P. Org. Lett. 2003, 5, 1229
22. Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333
23. Chan, A.; Scheidt, K. J. Am. Chem. Soc. 2006, 128, 4558
24. Willis, M. C. Angew. Chem., Int. Ed. 2010, DOI: 10.1002/anie.201000159.
25. For recent examples of transition-metal-catalyzed methods to access phthalides, please see: Everaere, K.; Scheffler, J.-L.; Mortreux, A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899
26. Witulski, B.; Zimmermann, A. Synlett 2002, 1855
27. Kawasaki, T.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2002, 67, 2653
28. Kosaka, M.; Sekiguchi, S.; Naito, J.; Uemura, M.; Kuwahara, S.; Watanabe, M.; Harada, N.; Hiroi, K. Chirality 2005, 17, 218
29. Tanaka, K.; Nishida, G.; Wada, A.; Noguchi, K. Angew. Chem., Int. Ed. 2004, 43, 6510
30. Cowell, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4193
31. Larock, R. C.; Fellows, C. A. J. Am. Chem. Soc. 1982, 104, 1900
32. Larock, R. C.; Fellows, C. A. J. Org. Chem. 1980, 45, 363
33. Rayabarapu, D. K.; Chang, H.-T.; Cheng, C.-H. Chem.-Eur. J. 2004, 10, 2991
34. Chang, H.-T.; Jeganmohan, M.; Cheng, C.-H. Chem.-Eur. J. 2007, 13, 4356
35. Shen, Z.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077
36. Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608
37. Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916
38. Xing, C.-H.; Liao, Y.-X.; He, P.; Hu, Q.-S. Chem. Commun. 2010, 46, 3010
39. Yamamoto, T.; Ohta, T.; Ito, Y. Org. Lett. 2005, 7, 4153
40. Suzuki, K.; Arao, T.; Ishii, S.; Maeda, Y.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2006, 47, 5789
41. Lin, S.; Lu, X. J. Org. Chem. 2007, 72, 9757
42. Qin, C.; Wu, H.; Cheng, J.; Chen, X.; Liu, M.; Zhang, W.; Su, W.; Ding, J. J. Org. Chem. 2007, 72, 4102
43. He, P.; Lu, Y.; Dong, C.-G.; Hu, Q.-S. Org. Lett. 2007, 9, 343
44. Kuriyama, M.; Shimazawa, R; Shirai, R. J. Org. Chem. 2008, 73, 1597
45. Liu, G.; Lu, X. J. Am. Chem. Soc. 2006, 128, 16504
46. Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Shirai, R.; Onomura, O. J. Org. Chem. 2009, 74, 9210
47. Ye, Z.; Lv, G.; Wang, W.; Zhang, M.; Cheng, J. Angew. Chem., Int. Ed. 2010, 49, 3671
48. Nagaki, A.; Kim, H.; Yoshida, J. Angew. Chem., Int. Ed. 2008, 47, 7833