Palladium(0)-catalyzed cyclization of 1,6-diyn-3-yl carbonates with a nucleophilic functionality: Efficient synthesis of polycyclic benzo[b]fluorene derivatives via allene intermediates

Organic and Biomolecular Chemistry

Volumn 10, Issue 18, 2012, Pages 3696-3704

  Zhu, Shugao ^a   Wu, Luling ^a   Huang, Xian ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EFFICIENT SYNTHESIS; FACILE METHOD; FLUORENE DERIVATIVES; TANDEM REACTION;

CARBONATES; CARBOXYLATION; CATALYSIS; FLUORINE CONTAINING POLYMERS;

CYCLIZATION;

BENZO[B]FLUORENE; CARBONIC ACID DERIVATIVE; FLUORENE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON;

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

CARBONATES; CATALYSIS; CYCLIZATION; FLUORENES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; POLYCYCLIC HYDROCARBONS, AROMATIC; STEREOISOMERISM;

EID: 84859868632     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob07148g     Document Type: Article

References (42)

1. H. E. Katz Z. Bao S. L. Gilat Acc. Chem. Res. 2001 34 359
2. C. D. Dimitrakopoulos P. R. L. Malenfant Adv. Mater. 2002 14 99
3. R. Freundenmann B. Behnisch M. Hanack J. Mater. Chem. 2001 11 1618
4. L. Schmidt-Mende A. Fechtenkötter K. Müllen E. Moons R. H. Friend J. D. MacKenzie Science 2001 293 1119
5. A. M. van de Craats N. Stutzmann O. Bunk M. M. Nielsen M. Watson K. Müllen H. D. Chanzy H. Sirringhaus R. H. Friend Adv. Mater. 2003 15 495
6. J. E. Anthony Angew. Chem., Int. Ed. 2008 47 452
7. W. Pisula X. Feng K. Müllen Chem. Rev. 2011 23 554
8. J. Wu W. Pisula K. Müllen Chem. Rev. 2007 107 718
9. B. R. Kaafarani Chem. Mater. 2011 23 378
10. S. J. Gould C. R. Melville M. C. Cone J. Chen J. R. Carney J. Org. Chem. 1997 62 320
11. Modern Allene Chemistry, ed., N. Krause, and, A. S. K. Hashmi, Wiley-VCH, Weinheim, 2004, vols. 1, 2
12. K. K. Wang Chem. Rev. 1996 96 207
13. J. A. Marshall Chem. Rev. 2000 100 3163
14. A. S. K. Hashmi Angew. Chem., Int. Ed. 2000 39 3590
15. R. Zimmer C. U. Dinesh E. Nandanan F. A. Khan Chem. Rev. 2000 100 3067
16. X. Lu C. Zhang Z. Xu Acc. Chem. Res. 2001 34 535
17. R. W. Bates V. Satcharoen Chem. Soc. Rev. 2002 31 12
18. S. Ma Acc. Chem. Res. 2003 36 701
19. L. K. Sydnes Chem. Rev. 2003 103 1133
20. L. Brandsma N. A. Nedolya Synthesis 2004 735
21. M. A. Tius Acc. Chem. Res. 2003 36 284
22. L. L. Wei H. Xiong R. P. Hsung Acc. Chem. Res. 2003 36 773
23. S. Ma, Palladium-Catalyzed Two or Three-Component Cyclization of Functionalized Allenes in Palladiumin Organic Synthesis, ed., J. Tsuji, Springer, Berlin, Heidelberg, 2005, pp. 183-210
24. S. Ma Chem. Rev. 2005 105 2829
25. S. Ma Aldrichimica Acta 2007 40 91
26. H. Kim L. J. Williams Curr. Opin. Drug Discovery Dev. 2008 11 870
27. M. Brasholz H.-U. Reissig R. Zimmer Acc. Chem. Res. 2009 42 45
28. S. Ma Acc. Chem. Res. 2009 42 1679
29. A. Hoffmann-Röder N. Krause Angew. Chem., Int. Ed. 2004 43 1196
30. N. Krause and A. Hoffmann-Röder, Chapter 18 in
31. G. Hu K. Liu L. Williams Org. Lett. 2008 10 5493
32. S. Wang W. Mao Z. She C. Li D. Yang Y. Lin L. Fu Bioorg. Med. Chem. Lett. 2007 17 2785
33. E. G. Lyakhova A. I. Kalinovsky A. S. Dmitrenok S. A. Kolesnikova S. N. Fedorov V. E. Vaskovsky V. A. Stonik Tetrahedron Lett. 2006 47 6549
34. X. Jiang C. Fu S. Ma Eur. J. Org. Chem. 2010 687
35. W. Kong C. Fu S. Ma Chem.-Eur. J. 2011 17 13134
36. R. Shen X. Huang Org. Lett. 2008 10 3283
37. R. Shen S. Zhu X. Huang J. Org. Chem. 2009 74 4118
38. R. Shen X. Huang L. Chen Adv. Synth. Catal. 2008 350 2865
39. F. Sha X. Huang Angew. Chem., Int. Ed. 2009 48 3458
40. X. Huang S. Zhu R. Shen Adv. Synth. Catal. 2009 351 3118
41. J. Cao X. Huang Org. Lett. 2010 12 5048
42. R. Shen X. Huang L. Chen Adv. Synth. Catal. 2009 351 2833