Palladium-Mediated Bis-Arylation of Inactivated and Activated Arenes

REFERENCES

• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Brossi , A. The Alkaloids ; Academic Press : Orlando , FL , 1985 .
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• Noyori , R. ; Takaya , H. BINAP: An efficient chiral element for asymmetric catalysis . Acc. Chem. Res. 1990 , 23 , 345 – 350 .
   Web of Science ®Google Scholar
• Diedrich , F. ; Stang , P. J. Metal-Catalyzed cross-coupling Reactions ; Wiley-VCH : New York , 1998 .
   Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Tsuji , J. Palladium Reagents and Catalysts ; John Wiley & Sons : New York , 2004 .
   Google Scholar
• Li , J. J. ; Gribble , G. W. Palladium in Heterocyclic Chemistry ; Pergamon : Oxford , 2000 .
   Google Scholar
• Echavarren , A. M. ; Gómez-Lor , B. ; González , J. ; de Frutos , Ó. Palladium-catalyzed intramolecular arylation reaction: Mechanism and application for the synthesis of polyarenes . Synlett . 2003 , 585 – 597 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• Ames , D. E. ; Opalko , A. Palladium-catalysed cyclisation of 2-substituted halogenoarenes by dehydrohalogenation . Tetrahedron. 1984 , 40 , 1919 – 1925 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• (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 π-deficient/π-excessive heteroaromatics: Synthesis of C-5 arylated imidazo[1,5-a]pyrazines . Org. Lett. 2008 , 10 , 2923 – 2926 ; (b) Turner , G. L. ; Morris , J. A. ; Greaney , M. F. Direct arylation of thiazoles on water . Angew. Chem., Int. Ed. 2007 , 46 , 7996 – 8000 ; (c) Parisien , M. ; Valette , D. ; Fagnou , K. Direct arylation reactions catalyzed by Pd(OH)2/C: Evidence for a soluble palladium catalyst . J. Org. Chem. 2005 , 70 , 7578 – 7584 .
   Google Scholar
• (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; (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; (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.
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• Strelitz , F. ; Flon , H. ; Weiss , U. ; Asheshov , D. N. Nybomycin, a new antibiotic with antiphage and antibacterial properties . Proc. Nat. Acad. Sci. USA. 1955 , 41 , 620 – 624 .
   Google Scholar
• Eble , T. E. ; Boyack , G. A. ; Large , C. M. ; Devries , W. H. Nybomycin: Isolation, properties, and derivatives . Antibiot. Chemother. 1958 , 8 , 627 – 630 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• Jouvenot , D. ; Glazer , E. C. ; Tor , Y. Photodimerizable ditopic ligand . Org. Lett . 2006 , 10 , 1987 – 1990 .
   Google Scholar
• Forbis , R. M. ; Rinehart Jr ., K. L. ; Nybomycin , VII: Preparative routes to nybomycin and deoxynybomycin . J. Am. Chem. Soc . 1973 , 95 , 5003 – 5013 .
   PubMed Web of Science ®Google Scholar