Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling

Tetrahedron Letters

Volumn 53, Issue 32, 2012, Pages 4173-4178

  Shen, Li ^a   Simmons, Charles J ^a   Sun, Dianqing ^a  

^a UNIVERSITY OF HAWAII AT HILO   (United States)

Author keywords

Bimolecular; Diaryl ether; Intramolecular; Macrocycle; Microwave assisted synthesis; Ullmann coupling

Indexed keywords

ETHER DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; MICROWAVE IRRADIATION; REACTION OPTIMIZATION; SYNTHESIS;

EID: 84863623735     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.142     Document Type: Article

References (31)

1. E.N. Pitsinos, V.P. Vidali, and E.A. Couladouros Eur. J. Org. Chem. 2011 2011 1207
2. V. Lakshmi Niranjan Reddy, K. Ravinder, M. Srinivasulu, T. Venkateshwar Goud, S. Malla Reddy, D. Srujankumar, T. Prabhakar Rao, U. Suryanarayana Murty, and Y. Venkateswarlu Chem. Pharm. Bull. 51 2003 1081
3. J. Lin, W. Zhang, N. Jiang, Z. Niu, K. Bao, L. Zhang, D. Liu, C. Pan, and X. Yao J. Nat. Prod. 71 2008 1938
4. S.V. Ley, and A.W. Thomas Angew. Chem., Int. Ed. 42 2003 5400
5. J.-F. Marcoux, S. Doye, and S.L. Buchwald J. Am. Chem. Soc. 119 1997 10539
6. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359
7. Q. Cai, B. Zou, and D. Ma Angew. Chem. 118 2006 1298
8. C.H. Burgos, T.E. Barder, X. Huang, and S.L. Buchwald Angew. Chem., Int. Ed. 45 2006 4321
9. D. Ma, and Q. Cai Org. Lett. 5 2003 3799
10. L. Salvi, N.R. Davis, S.Z. Ali, and S.L. Buchwald Org. Lett. 14 2012 170
11. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250
12. M. Larhed, C. Moberg, and A. Hallberg Acc. Chem. Res. 35 2002 717
13. D. Dallinger, and C.O. Kappe Chem. Rev. 107 2007 2563
14. A. Lew, P.O. Krutzik, M.E. Hart, and A.R. Chamberlin J. Comb. Chem. 4 2001 95
15. H. He, and Y.-J. Wu Tetrahedron Lett. 44 2003 3445
16. Y. Baqi, and C.E. Müller Org. Lett. 9 2007 1271
17. N.D. D'Angelo, J.J. Peterson, S.K. Booker, I. Fellows, C. Dominguez, R. Hungate, P.J. Reider, and T.-S. Kim Tetrahedron Lett. 47 2006 5045
18. B.H. Lipshutz, J.B. Unger, and B.R. Taft Org. Lett. 9 2007 1089
19. R.N. Chapman, and P.S. Arora Org. Lett. 8 2006 5825
20. C. Pérez-Balado, A. Nebbioso, P. Rodríguez-Graña, A. Minichiello, M. Miceli, L. Altucci, and Á.R. de Lera J. Med. Chem. 50 2007 2497
21. A. Afonso, L. Feliu, and M. Planas Tetrahedron 67 2011 2238
22. E. Cini, C.B. Botta, M. Rodriquez, and M. Taddei Tetrahedron Lett. 50 2009 7159
23. E. Nnanabu, and K. Burgess Org. Lett. 8 2006 1259
24. L. Shen, and D. Sun Tetrahedron Lett. 52 2011 4570
25. V.C. Bryant, G.D. Kishore Kumar, A.M. Nyong, and A. Natarajan Bioorg. Med. Chem. Lett. 22 2012 245
26. G.D. Kishore Kumar, and A. Natarajan Tetrahedron Lett. 49 2008 2103
27. For related observations with a bimolecular cyclization lactone product, see: A. Nakahara, M. Kanbe, and M. Nakada Tetrahedron Lett. 53 2012 1518
28. For a bimolecular cyclization lactam product, see: D.L. Boger, D. Yohannes, J. Zhou, and M.A. Patane J. Am. Chem. Soc. 115 1993 3420
29. A. Pinto, M. Wang, M. Horsman, and C.N. Boddy Org. Lett. 14 2012 2278
30. C.C. Aldrich, L. Venkatraman, D.H. Sherman, and R.A. Fecik J. Am. Chem. Soc. 127 2005 8910
31. A lower yield at higher concentration was also noted previously in the synthesis of a similar ring-closing system by the Zhu group, see: G.I. Gonzalez, and J. Zhu J. Org. Chem. 64 1999 914