Palladium-Catalyzed Cross-Coupling of 2,3-Naphthoxadisilole with Aryl Halides

REFERENCES

• (a) 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 – 1469 ; (b) Negishi , E.-I. ; de Meijere , A. (Eds.). Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002 .
   PubMed Web of Science ®Google Scholar
• (a) Nicolaou , K. C. ; Boddy , C. N. C. ; Brase , S. ; Winssinger , N. Chemistry, biology, and medicine of the glycopeptide antibiotics . Angew. Chem. Int. Ed. 1999 , 38 , 2096 – 2152 ; (b) Pu , L. 1,1′-Binaphthyl dimers, oligomers, and polymers: Molecular recognition, asymmetric catalysis, and new materials . Chem. Rev. 1998 , 98 , 2405 – 2494 ; (c) Littke , A. F. ; Fu , G. C. Palladium-catalyzed coupling reactions of aryl chlorides . Angew. Chem. Int. Ed. 2002 , 41 , 4176 – 4211 ; (d) Nakao , Y. ; Sahoo , A. K. ; Yada , A. ; Chen , J. S. ; Hiyama , T. Biaryl synthesis using highly stable aryl[2-(hydroxymethyl)phenyl]dimethylsilanes and aryl iodides under fluoride-free conditions . Sci. Technol. Adv. Mater. 2006 , 7 , 536 – 543 ; (e) Shi , S. Y. ; Zhang , Y. H. Pd(Oac)2–catalyzed fluoride-free cross-coupling reactions of arylsiloxanes with aryl bromides in aqueous medium . J. Org. Chem. 2007 , 72 , 5927 – 5930 .
   PubMed Web of Science ®Google Scholar
• (a) Milstein , D. ; Stille , J. K. Palladium-catalyzed coupling of tetraorganotin compounds with aryl and benzyl halides: Synthetic utility and mechanism . J. Am. Chem. Soc. 1979 , 101 , 4992 – 4998 ; (b) Stille , J. K. The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles . Angew. Chem., Int. Ed. Engl. 1986 , 25 , 508 – 524 ; (c) Handy , S. T. ; Zhang , X. Organic synthesis in ionic liquids: The stille coupling . Org. Lett. 2001 , 3 , 233 – 236 ; (d) Espinet , P. ; Echavarren , A. M. The mechanisms of the stille reaction . Angew. Chem., Int. Ed. 2004 , 43 , 4704 – 4734 .
   Web of Science ®Google Scholar
• (a) Miyaura , N. ; Suzuki , A. Palladium-catalyzed cross-coupling reactions of organoboron compounds . Chem. Rev. 1995 , 95 , 2457 – 2483 ; (b) Suzuki , A. In Metal-Catalyzed Cross-Coupling Reactions; F. Diederich, P. J. Stang (Eds.); Wiley-VCH: Weinheim, 1998; p. 49 ; (c) Suzuki , A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998 . J. Organomet. Chem. 1999 , 576 , 147 – 168 ; (d) Miao , W. ; Chan , T. H. Exploration of ionic liquids as soluble supports for organic synthesis: Demonstration with a Suzuki coupling reaction . Org. Lett. 2003 , 5 , 5003 – 5005 ; (e) Xiao , J. C. ; Shreeve , J. M. Synthesis of 2,2′-Biimidazolium-based ionic liquids: Use as a new reaction medium and ligand for palladium-catalyzed Suzuki cross-coupling reactions . J. Org. Chem. 2005 , 70 , 3072 – 3078 .
   Web of Science ®Google Scholar
• Hall , D. G. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine ; Wiley-VCH : Weinheim , 2005; pp. 1–99.
   Google Scholar
• (a) Denmark , S. E. ; Sweis , R. F. In Metal-Catalyzed Cross-Coupling Reactions, , 2nd ed. ; A. de Meijere , F. Diederich (Eds.); Wiley-VCH : Weinheim , Germany , 2004 ; pp. 163 – 216 ; (b) Tsuji , J. In Palladium Reagents and Catalysts ; John Wiley & Sons : Chichester , UK , 2004 ; pp. 338 – 351 ; (c) Nakao , Y. ; Imanaka , H. ; Sahoo , A. K. ; Yada , A. ; Hiyama , T. Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilic on reagents for the silicon-based cross-coupling reaction. J. Am. Chem. Soc. 2005, 127, 6952–6953 .
   Google Scholar
• (a) Hiyama , T. ; Shirakawa , E. Organosilicon compounds ; In Cross-Coupling Reactions: A Practical Guide ; N. Miyaura (Ed.); Springer : Berlin , 2002 ; p. 61 ; (b) Denmark , S. E. ; Sweiss , R. F. Design and implementation of new, silicon-based, cross-coupling reactions: Importance of silicon-oxygen bonds. Acc. Chem. Res. 2002, 35, 835–846 ; (c) Denmark , S. E. ; Baird , J. D. Palladium-catalyzed cross-coupling reactions of silanolates: A paradigm shift in silicon-based cross-coupling reactions. Chem. Eur. J. 2006, 12, 4954–4963 ; (d) Endo , M. ; Sakurai , T. ; Ojima , S. ; Katayama , T. ; Unno , M. ; Matsumoto , H. ; Kowase , S. ; Sano , H. ; Kosugi , M. ; Fugami , K. Novel palladium-catalyzed atom-efficient cross-coupling reaction by means of hexaarylcyclotrisiloxane. Synlett 2007, 749–752 ; (e) Seganish , W. M. ; Deshong , P. Palladium-catalyzed cross-coupling of aryl triethyl ammonium bis(catechol) silicates with aryl bromides using microwave irradiation. Org. Lett. 2004, 6, 4379–4381 ; (f) Handy , C. J. ; Manoso , A. S. ; McElroy , W. T. ; Seganish , W. M. ; Deshong , P. Recent advances in siloxane-based aryl–aryl coupling reactions: Focus on heteroaromatic systems. Tetrahedron 2005, 61, 12201–12225 ; (g) Hirabayashi , K. ; Mori , A. ; Kawashima , J. ; Suguro , M. ; Nishihara , Y. ; Hiyama , T. Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide. J. Org. Chem. 2000, 65, 5342–5349 ; (h) Denmark , S. E. ; Ober , M. H. Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols. Adv. Synth. Catal. 2004, 346, 1703–1714 ; (i) Napier , S. ; Marcuccio , S. M. ; Tye , H. ; Whittaker , M. A robust method for the Hiyama-type coupling of arylsiloxanes and disiloxanes with aryl halides. Tetrahedron Lett. 2008, 49, 3939–3942 ; (j) Murata , M. ; Yoshida , S. ; Nirei , S. I. ; Watanabe , S. J. ; Masuda , Y. An efficient catalyst system for palladium(0)-catalyzed cross-coupling of aryltrialkoxysilanes with aryl halides. Synlett 2006, 1, 118–120 ; (k) Denmark , S. E. ; Regens , C. S. Palladium-catalyzed cross-coupling reactions of organosilanols and their salts: Practical alternatives to boron- and tin-based methods. Acc. Chem. Res. 2008, 41, 1486–1499 .
   Google Scholar
• (a) Chen , Y. L. ; Sun , J. Q. ; Wei , X. ; Yang , W. Y. ; Lee , A. W. M. Generation of synthetic equivalents of benzdiynes from benzobisoxadisiloles . J. Org. Chem. 2004 , 69 , 7190 – 7197 ; (b) Chen , Y. L. ; Hau , C. K. ; Wang , H. ; He , H. ; Wong , M. S. ; Lee , A. W. M. Oxadisilole fused isobenzofurans: Synthesis and characterization of oxadisilole substituted acenes . J. Org. Chem. 2006 , 71 , 3512 – 3517 ; (c) Chen , Y. L. ; Zhang , H. ; Wong , W. Y. ; Lee , A. W. M. Cycloaddition reactions of benzynes generated from benzobisoxadisilole, benzotrisoxadisilole, and naphthoxadisilole . Tetrahedron Lett. 2002 , 43 , 2259 – 2262 .
   Google Scholar
• Hatanaka , Y. ; Goda , K. ; Hiyama , T. On the regioselectivity of palladium-catalyzed cross-coupling reactions of alkenylsilanes: Participation of β-cationic organosilicate-palladium species during the transmetallation . J. Organomet. Chem. 1994 , 465 , 97 – 100 .
   Google Scholar
• Chuit , C. ; Corriu , R. J. P. ; Reye , C. In Chemistry of Hypervalent Compounds ; K.-Y. Akiba (Ed.); Wiley-VCH : New York , 1999 ; pp. 81 – 146 .
   Google Scholar
• (a) Duan , J. P. ; Cheng , C. H. Palladium-catalyzed reductive couplings of organic halides with 7-heteroatom norbornadienes: New synthetic methods for substituted aryls and cis-1,2-dihydro-l-naphthyl alcohols and carbamates. Organometallics 1995, 14, 1608–1618; (b) Brito , C. M. ; Pinto , D. C. G. A. ; Silva , A. M. S. ; Silva , A. M. G. ; Tome , A. C. ; Cavaleiro , J. A. S. Diels–Alder reactions of 2′-hydroxychalcones with ortho-benzoquino-methane: A new synthesis of 3-aryl-2-naphthyl 2-hydroxyphenyl ketones. Eur. J. Org. Chem. 2006, 2558–2569; (c) Rao , M. N. ; Jadhav , D. N. ; Banerjee , D. A new palladium-catalyzed protocol for atom-efficient cross-coupling reactions of triarylbismuths with aryl halides and triates. Tetrahedron 2008, 64, 5762–5772; (d) Kuriyama , M. ; Shimazawa , R. ; Shirai , R. Design and synthesis of thioether-imidazolium chlorides as efficient ligands for palladium-catalyzed Suzuki–Miyaur coupling of aryl bromides with arylboronic acids. Tetrahedron 2007, 63, 9393–9400.
   Google Scholar
• Wipf , P. ; Jung , J. K. Formal Tota synthesis of (+)-diepoxin σ . J. Org. Chem. 2000 , 65 , 6319 – 6337 .
   PubMed Web of Science ®Google Scholar