Exploiting the versatility of organometallic cross-coupling reactions for entry into extended aromatic systems
作者： John D Tovar , Timothy M Swager
DOI: 10.1016/S0022-328X(02)01166-X
关键词: Combinatorial chemistry 、 Organic chemistry 、 Chemistry 、 Electrophile 、 Coupling reaction
摘要: Using a variety of Pd-catalyzed cross-coupling techniques, we have prepared several pendant arene derivatives (5, 6, 12, 15). From these materials, expanded upon earlier work and developed new electrophilic cyclization strategies. By employing sufficiently strong electrophile sources, may efficiently effect double annulations to afford polycyclic aromatics 10, 11, 13 16. This chemistry allows for the participation both heteroaromatic heteroatomic moieties thus providing an electronically diverse array extended aromatic systems.
elsevier.com
sci-hub.se 参考文章(21)
Arnulf-Dieter Schlüter, Ladder Polymers: The new generation Advanced Materials. ,vol. 3, pp. 282- 291 ,(1991) , 10.1002/ADMA.19910030603
Jeff D. Debad, Allen J. Bard, Electropolymerization of Acenaphtho[1,2-k]fluoranthene Derivatives: Formation of a New Conductive Electroactive Electrochromic Hydrocarbon Ladder Polymer Journal of the American Chemical Society. ,vol. 120, pp. 2476- 2477 ,(1998) , 10.1021/JA973831M
Igor A. Levitsky, Jinsang Kim, Timothy M. Swager, Energy Migration in a Poly(phenylene ethynylene): Determination of Interpolymer Transport in Anisotropic Langmuir−Blodgett Films Journal of the American Chemical Society. ,vol. 121, pp. 1466- 1472 ,(1999) , 10.1021/JA982610T
N. Miyaura, T. Yanagi, A. Suzuki, The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases Synthetic Communications. ,vol. 11, pp. 513- 519 ,(1981) , 10.1080/00397918108063618
Qin Zhou, Timothy M. Swager, Fluorescent Chemosensors Based on Energy Migration in Conjugated Polymers: The Molecular Wire Approach to Increased Sensitivity Journal of the American Chemical Society. ,vol. 117, pp. 12593- 12602 ,(1995) , 10.1021/JA00155A023
Marc B. Goldfinger, Khushrav B. Crawford, Timothy M. Swager, Directed Electrophilic Cyclizations: Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics Journal of the American Chemical Society. ,vol. 119, pp. 4578- 4593 ,(1997) , 10.1021/JA9642673
Kenkichi Sonogashira, Yasuo Tohda, Nobue Hagihara, A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines Tetrahedron Letters. ,vol. 16, pp. 4467- 4470 ,(1975) , 10.1016/S0040-4039(00)91094-3
A.-D. Schlüter, M. Löffler, V. Enkelmann, Synthesis of a fully unsaturated all-carbon ladder polymer Nature. ,vol. 368, pp. 831- 834 ,(1994) , 10.1038/368831A0
D. Milstein, J. K. Stille, Palladium-catalyzed coupling of tetraorganotin compounds with aryl and benzyl halides. Synthetic utility and mechanism Journal of the American Chemical Society. ,vol. 10, pp. 4992- 4998 ,(1979) , 10.1021/JA00511A032
Jinsang Kim, Sean K. McHugh, Timothy M. Swager, Nanoscale fibrils and grids : Aggregated structures from rigid-rod conjugated polymers Macromolecules. ,vol. 32, pp. 1500- 1507 ,(1999) , 10.1021/MA981774R