Palladium-mediated bis-arylation of inactivated and activated arenes

Synthetic Communications

Volumn 41, Issue 1, 2011, Pages 121-130

  Majumdar, Krishna C ^a   De, Nirupam ^a   Chakravorty, Santanu ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Biaryl coupling; bis cyclization; palladium acetate; pyridonaphthyridinedione; pyridoquinolinedione

Indexed keywords

NITROGEN; PALLADIUM ACETATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CYCLIZATION;

EID: 78650376927     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903531870     Document Type: Article

References (36)

1. Park, C. H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Palladium-catalyzed arylation and heteroarylation of indolizines. Org. Lett. 2004, 6, 1159-1162.
2. Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. Oxidative C H activation/C- C bond forming reactions: Synthetic scope and mechanistic insights. J. Am. Chem. Soc. 2005, 127, 7330-7331.
3. Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. Pd-catalyzed alkyl to aryl migration and cyclization: An efficient synthesis of fused polycycles via multiple C H activation. J. Am. Chem. Soc. 2004, 126, 7460-7461.
4. Rama Rao, A. V.; Gurjar, M. K.; Reddy, L.; Srinivasa Rao, A. Studies directed toward the synthesis of vancomycin and related cyclic peptides. Chem. Rev. 1995, 95, 2135-2167.
5. Brossi, A. The Alkaloids; Academic Press: Orlando, FL, 1985.
6. Rosini, C; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis and applications of binaphthylic C2-symmetry derivatives as chiral auxiliaries in enantioselective reactions. Synthesis. 1992, 503-516.
7. Noyori, R.; Takaya, H. BINAP: An efficient chiral element for asymmetric catalysis. Acc. Chem. Res. 1990, 23, 345-350.
8. Diedrich, F.; Stang, P. J. Metal-Catalyzed cross-coupling Reactions; Wiley-VCH: New York, 1998.
9. Hassan, J.; Sevignon, M.; Gozzi, C; Schulz, E.; Lemaire, M. Aryl- aryl bond formation one century after the discovery of the Ullmann reaction. Chem. Rev. 2002,102, 1359-1470.
10. Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 2004.
11. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Oxford, 2000.
12. Echavarren, A. M.; Gomez-Lor, B.; Gonzalez, J.; de Frutos, O. Palladium-catalyzed intramolecular arylation reaction: Mechanism and application for the synthesis of polyar-enes. Synlett. 2003, 585-597.
13. Harayama, T.; Akamatsu, H.; Okamura, K.; Miyagoe, T.; Akiyama, T.; Abe, H.; Takeuchi, Y. Synthesis of trisphaeridine and norvhelerythrine through palladium-catalyzed aryl-aryl coupling reactions. J. Chem. Soc, Perkin Trans. 1 2001, 9, 523-528.
14. Majumdar, K. C; Pal, A. K.; Taher, A.; Debnath, P. Highly effective regioselective method for the synthesis of substituted coumarin and quinolone annulated heterocycles using Pd(0)-catalyzed reaction. Synthesis 2007, 1707-1711.
15. Majumdar, K. C; Debnath, P.; Taher, A.; Pal, A. K. Intramolecular cyclization reaction: Palladium(0)-catalyzed cyclization is more effective than tin hydride-mediated reaction. Can. J. Chem. 2008, 86, 325-332.
16. Majumdar, K. C; Chattopadhyay, B.; Taher, A. New efficient synthesis of pyrido[2,3-c]-coumarin derivatives by the Pd-catalyzed Heck cyclization. Synthesis. 2007, 3647-3652.
17. Majumdar, K. C; Taher, A.; Debnath, P. Palladium-catalyzed intramolecular biaryl coupling: A highly efficient avenue for benzannulated pyranoquinolines and julolidine derivatives. Synthesis. 2009, 793-800.
18. Majumdar, K. C; Chattopadhyay, B.; Pal, A. K. Regioselective synthesis of coumarin and quinolone-annulated linearly fused heterocycles by intramolecular Heck reaction of biaryl systems. Org. Chem. Lett. 2008, 5, 276-281.
19. Ames, D. E.; Opalko, A. Palladium-catalysed cyclisation of 2-substituted halogenoarenes by dehydrohalogenation. Tetrahedron. 1984, 40, 1919-1925.
20. Kuroda, T.; Suzuki, F. Synthesis of 1H-imidazo[4,5-c]quinolin-4(5H)-one via palladium-catalyzed cyclization of N-(2-bromophenyl)-1H-imidazole-4- carboxamide. Tetrahedron Lett. 1991, 32, 6915-6918.
21. Goswami, S. P.; Adak, A. K.; Mukherjee, R.; Jana, S.; Dey, S.; Gallagher, J. F. A convenient palladium-catalyzed synthesis of symmetric biaryls, biheterocycles, and biaryl chiral diamides. Tetrahedron. 2005, 61, 4289-4295.
22. (a) Wang, J.-X.; McCubbin, J. A.; Jin, M.; Laufer, R. S.; Mao, Y.; Crew, A. P.; Mulvihill, M. J.; Snieckus, V. Palladium-catalyzed direct Heck arylation of dual 7i-deficient/ 7i-excessive heteroaromatics: Synthesis of C-5 arylated imidazo[1,5-a]pyrazines. Org. Lett. 2008, 10, 2923-2926;
23. (b) Turner, G. L.; Morris, J. A.; Greaney, M. F. Direct arylation of thiazoles on water. Angew. Chem., Int. Ed. 2007, 46, 7996-8000;
24. 2/C: Evidence for a soluble palladium catalyst. J. Org. Chem. 2005, 70, 7578-7584.
25. (a) Caron, L.; Campeau, L.-C; Fagnou, K. Palladium-catalyzed direct arylation of nitro-substituted aromatics with aryl halides. Org. Lett. 2008,10, 4533-4536;
26. (b) Bernini, R.; Cacchi, S.; Fabrizi, G.; Sferrazza, A. A simple general approach to phenanthridinones via palladium-catalyzed intramolecular direct arene arylation. Synthesis. 2008, 729-738;
27. (c) Campeau, L.-C; Parisien, M.; Leblanc, M.; Fagnou, K. Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes. J. Am. Chem. Soc. 2004, 126, 9186-9187.
28. Jhu, S.; Ruchelman, A. L.; Zhau, N.; Liu, A.; Liu, L. F.; LaVoie, E. J. 6-Substituted 6H-dibenzo[c,h][2,6]naphthyridin-5-ones: Reversed lactam analogues of ARC-111 with potent topoisomerase I-targeting activity and cytotoxicity. Bioorg. Med. Chem. 2006, 14, 3131-3143.
29. Leclerc, J. P.; Fagnou, K. Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides. Angew. Chem., Int. Ed. 2006, 45, 7781-7786.
30. Strelitz, F.; Flon, H.; Weiss, U.; Asheshov, D. N. Nybomycin, a new antibiotic with anti-phage and antibacterial properties. Proc. Nat. Acad. Sci. USA. 1955, 41, 620-624.
31. Eble, T. E.; Boyack, G. A.; Large, C. M.; Devries, W. H. Nybomycin: Isolation, properties, and derivatives. Antibiot. Chemother. 1958, 8, 627-630.
32. Asahara, M.; Shibano, C.; Koyama, K.; Tamura, M.; Tohda, Y.; Nishiwaki, N.; Ariga, M. The nitroalkene showing dual behaviors in the same reaction system. Tetrahedron Lett. 2005, 46, 7519-7521.
33. Majumdar, K. C.; Chakravorty, S.; De, N. Palladium-mediated bis- and tris-biaryl Heck coupling for the synthesis of heterocycles. Tetrahedron Lett. 2008, 49, 3419-3422.
34. Majumdar, K. C.; Chattopadhyay. B.; Chakravorty, S. An expedient palladium-mediated intramolecular cyclization route to the synthesis of bis-fused benzofuran and a two-directional ring closing metathesis for the synthesis of bis-oxepin and bis-benzoxocine. Synthesis. 2009, 674-680.
35. Jouvenot, D.; Glazer, E. C.; Tor, Y. Photodimerizable ditopic ligand. Org. Lett. 2006, 10, 1987-1990.
36. Forbis, R. M.; Rinehart Jr., K. L.; Nybomycin, VII: Preparative routes to nybomycin and deoxynybomycin. J. Am. Chem. Soc. 1973, 95, 5003-5013.