PPh3-mediated intramolecular conjugation of alkyl halides with electron-deficient olefins: Facile synthesis of chromans and relevant analogues

Chemical Communications

Volumn 49, Issue 40, 2013, Pages 4570-4572

  Zhu, Jian Bo ^a   Wang, Peng ^a   Liao, Saihu ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CHROMAN DERIVATIVE; HALOGENATED HYDROCARBON; PHOSPHINE; PHOSPHINE DERIVATIVE; FIBRINOGEN RECEPTOR ANTAGONIST; HALIDE; HALOGENOALKANE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; SYNTHESIS; CHEMICAL REACTION; CONJUGATION; CYCLIZATION; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; THROMBOSIS;

ALKENES; CHROMANS; ELECTRONS; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; PHOSPHINES;

EID: 84876928524     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc41435c     Document Type: Article

References (40)

1. M. B. Smith and J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley-Interscience, New York, 6th edn, 2007
2. C. J. Rosenker and P. Wipf, in The Chemistry of Organocopper Compounds, Part 2, ed. Z. Rappoport and I. Marek, John Wiley & Sons Ltd., Chichester, 2009, pp. 443-525
3. B. H. Lipshutz, S. Huang, W. W. Y. Leong, G. Zhong, N. A. Isley: J. Am. Chem. Soc. 2012 134:19985-19988
4. D. Badone, J. Bernassau, R. Cardamone, U. Guzzi: Angew. Chem., Int. Ed. 1996 35:535-538
5. G. Wu, F. Lamaty, E. Negishi: J. Org. Chem. 1989 54:2507-2508
6. G. Just, G. Sacripante: Can. J. Chem. 1987 65:104-109
7. B. Giese, B. Kopping, T. GÖbel, J. Dickhaut, G. Thoma, K. J. Kulicke and F. Trach, Radical Cyclization Reactions, Organic Reactions, 2004, pp. 301-856
8. E. J. Enholm, J. S. Cottone, F. Allais: Org. Lett. 2001 3:145-147
9. N. Maulide, I. E. Markó: Chem. Commun. 2006 1200-1202
10. D. L. J. Clive, R. Sunasee: Org. Lett. 2007 9:2677-2680
11. D. L. J. Clive, R. Sunasee, Z. Chen: Org. Biomol. Chem. 2008 6:2434-2441
12. H. Kim, C. Lee: Org. Lett. 2011 13:2050-2053
13. X.-L. Sun, Y. Tang: Acc. Chem. Res. 2008 41:937-948
14. Y. Tang, S. Ye, X.-L. Sun: Synlett 2005 2720-2730
15. X.-M. Deng, P. Cai, S. Ye, X.-L. Sun, W.-W. Liao, K. Li, Y. Tang, Y.-D. Wu, L.-X. Dai: J. Am. Chem. Soc. 2006 128:9730-9740
16. L.-W. Ye, X.-L. Sun, C.-Y. Zhu, Y. Tang: Org. Lett. 2006 8:3853-3856
17. L.-W. Ye, X.-L. Sun, Q.-G. Wang, Y. Tang: Angew. Chem., Int. Ed. 2007 46:5951-5954
18. Q.-G. Wang, X.-M. Deng, B.-H. Zhu, L.-W. Ye, X.-L. Sun, C.-Y. Li, C.-Y. Zhu, Q. Shen, Y. Tang: J. Am. Chem. Soc. 2008 130:5408-5409
19. C.-Y. Zhu, X.-Y. Cao, B.-H. Zhu, C. Deng, X.-L. Sun, B.-Q. Wang, Q. Shen, Y. Tang: Chem.-Eur. J. 2009 15:11465-11468
20. A. Schnell, J. C. Tebby: Chem. Commun. 1977 1883-1886
21. E. Taylor, S. F. Martin: J. Am. Chem. Soc. 1974 96:8095-8102
22. F. Zaragoza: J. Org. Chem. 2002 67:4963-4964
23. Y. J. Im, J. E. Na, J. N. Kim: Bull. Korean Chem. Soc. 2003 24:511-513
24. K. Y. Lee, J. E. Na, M. J. Lee, J. N. Kim: Tetrahedron Lett. 2004 45:5977-5981
25. D. Duvvuru, P. Retailleau, J.-F. Betzer, A. Marinetti: Eur. J. Org. Chem. 2012 897-900
26. O. I. Kolodiazhnyi, Phosphorus Ylides: Chemistry and Application in Organic Synthesis, Wiley-VCH, Weinheim, 1999, pp. 84-87
27. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 5
28. L. Zu, S. Zhang, H. Xie, W. Wang: Org. Lett. 2009 11:1627-1630
29. B. M. Trost, H. C. Shen, L. Dong, J.-P. Surivet, C. Sylvain: J. Am. Chem. Soc. 2004 126:11966-11983
30. W. A. Kinney, C. A. Teleha, A. S. Thompson, M. Newport, R. Hansen, S. Ballentine, S. Ghosh, A. Mahan, G. Grasa, A. Zanotti-Gerosa, J. Dingenen, C. Schubert, Y. Zhou, G. C. Leo, D. F. McComsey, R. J. Santulli, B. E. Maryanoff: J. Org. Chem. 2008 73:2302-2310
31. Y. Kanbe, M.-H. Kim, M. Nishimoto, Y. Ohtake, N. Kato, T. Tsunenari, K. Taniguchi, I. Ohizumi, S. Kaiho, K. Morikawa, J.-C. Jo, H.-S. Lim, H.-Y. Kim: Bioorg. Med. Chem. 2006 14:4803-4819
32. M. E. Krafft, K. A. Seibert, T. F. N. Haxell, C. Hirosawa: Chem. Commun. 2005 5772-5774
33. M. E. Krafft, T. F. N. Haxell, K. A. Seibert, K. A. Abboud: J. Am. Chem. Soc. 2006 128:4174-4175
34. C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu: J. Am. Chem. Soc. 2006 128:1472-1473
35. L. Zhao, X. Y. Chen, S. Ye, Z.-X. Wang: J. Org. Chem. 2011 76:2733-2743
36. H. C. Shen: Tetrahedron 2009 65:3931-3952
37. X.-M. Cheng, G. F. Filzen, A. G. Geyer, C. Lee and B. K. Trivedi, US 0207915, 2003
38. K. Okumura, T. Shimazaki, Y. Aoki, H. Yamashita: J. Med. Chem. 1998 41:4036-4052
39. Mitsui Toatsu Chemicals, Inc., US 5629321, 1997
40. Mitsui Toatsu Chemicals, Inc., EP 760364, 1997