Synthesis and characterization of hexaarylbenzenes with five or six different substituents enabled by programmed synthesis

Nature Chemistry

Volumn 7, Issue 3, 2015, Pages 227-233

  Suzuki, Shin ^a   Segawa, Yasutomo ^a   Itami, Kenichiro ^a   Yamaguchi, Junichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84923374339     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2174     Document Type: Article

References (50)

1. Faraday, M. On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat. Phil. Trans. R. Soc. Lond. 115, 440-466 (1825).
2. Taylor, R. D., MacCoss, M. & Lawson, A. D. G. Rings in drugs. J. Med. Chem. 57, 5845-5859 (2014).
3. Burnside, W. Theory of Groups of Finite Order (Cambridge Univ. Press, 1897).
4. Polya, G. & Reade, R. C. Combinatorial Enumerations of Groups, Graphs, and Chemical Compounds (Springer, 1987).
5. Hoye, T. R., Baire, B., Niu, D., Willoughby, P. H. & Woods, B. P. The hexadehydro-Diels-Alder reaction. Nature 490, 208-212 (2012).
6. Itami, K. & Yoshida, J. Platform synthesis: a useful strategy for rapid and systematic generation of molecular diversity. Chem. Eur. J. 12, 3966-3974 (2006).
7. Itami, K. et al. Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-Pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis. J. Am. Chem. Soc. 123, 11577-11585 (2001).
8. Itami, K., Ohashi, Y. & Yoshida, J. Triarylethene-based extended π-systems: programmable synthesis and photophysical properties. J. Org. Chem. 70, 2778-2792 (2005).
9. Itami, K., Tonogaki, K., Nokami, T., Ohashi, Y. & Yoshida, J. Palladiumcatalyzed convergent synthesis and properties of conjugated dendrimers based on triarylethene branching. Angew. Chem. Int. Ed. 45, 2404-2409 (2006).
10. Itami, K., Mineno, M., Muraoka, N. & Yoshida, J. Sequential assembly strategy for tetrasubstituted olefin synthesis using vinyl 2-pyrimidyl sulfide as a platform. J. Am. Chem. Soc. 126, 11778-11779 (2004).
11. Itami, K., Kamei, T. & Yoshida, J. Diversity-oriented synthesis of tamoxifen-type tetrasubstituted olefins. J. Am. Chem. Soc. 125, 14670-14671 (2003).
12. Itami, K., Yamazaki, D. & Yoshida, J. Pyrimidine-core extended π-systems: general synthesis and interesting fluorescent properties. J. Am. Chem. Soc. 126, 15396-15397 (2004).
13. Yanagisawa, S., Ueda, K., Sekizawa, H. & Itami, K. Programmed synthesis of tetraarylthiophenes through sequential C-H arylation. J. Am. Chem. Soc. 131, 14622-14623 (2009).
14. Tani, S., Uehara, T. N., Yamaguchi, J. & Itami, K. Programmed synthesis of arylthiazoles through sequential C-H couplings. Chem. Sci. 5, 123-135 (2014).
15. Geng, Y., Fechtenkötter, A. & Müllen, K. Star-like substituted hexaarylbenzenes: synthesis and mesomorphic properties. J. Mater. Chem. 11, 1634-1641 (2001).
16. Tomović, Z. et al. Star-shaped oligo(p-phenylenevinylene) substituted hexaarylbenzene: purity, stability, and chiral self-assembly. J. Am. Chem. Soc. 129, 16190-16196 (2007).
17. Kobayashi, K., Sato, A., Sakamoto, S. & Yamaguchi, K. Solvent-induced polymorphism of three-dimensional hydrogen-bonded networks of hexakis(4-carbamoylphenyl)benzene. J. Am. Chem. Soc. 125, 3035-3045 (2003).
18. Hiraoka, S., Nakamura, T., Shiro, M. & Shionoya, M. In-water truly monodisperse aggregation of gear-shaped amphiphiles based on hydrophobic surface engineering. J. Am. Chem. Soc. 132, 13223-13225 (2010).
19. II dodecanuclear quadruple-decker complex with three rotors. Angew. Chem. Int. Ed. 49, 1669-1673 (2010).
20. Steeger, M. & Lambert, C. Charge-transfer interactions in tris-donor-tris-acceptor hexaarylbenzene redox chromophores. Chem. Eur. J. 18, 11937-11948 (2012).
21. Traber, B. et al. Hexasubstituted donor-acceptor benzenes as nonlinear optically active molecules with multiple charge-transfer transitions. Chem. Eur. J. 10, 1227-1238 (2004).
22. Tanaka, Y., Koike, T. & Akita, M. 2-Dimensional molecular wiring based on toroidal delocalization of hexaarylbenzene. Chem. Commun. 46, 4529-4531 (2010).
23. + for effective cation-π interaction. J. Am. Chem. Soc. 128, 5328-5329 (2006).
24. Chen, L., Hernandez, Y., Feng, X. & Müllen, K. From nanographene and graphene nanoribbons to graphene sheets: chemical synthesis. Angew. Chem. Int. Ed. 51, 7640-7654 (2012).
25. Seyler, H., Purushothaman, B., Jones, D. J., Holmes, A. B. & Wong, W. W. H. Hexa-peri-hexabenzocoronene in organic electronics. Pure Appl. Chem. 84, 1047-1067 (2012).
26. Zhang, W. et al. Supramolecular linear heterojunction composed of graphite-like semiconducting nanotubular segments. Science 334, 340-343 (2011).
27. Campeau, L-C. et al. C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions. J. Am. Chem. Soc. 130, 3276-3277 (2008).
28. Campeau, L-C. et al. Palladium-catalyzed direct arylation of azine and azole N-oxides: reaction development, scope and applications in synthesis. J. Am. Chem. Soc. 131, 3291-3306 (2009).
29. Joo, J. M., Touré, B. B. & Sames, D. C-H bonds as ubiquitous functionality a general approach to complex arylated imidazoles via regioselective sequential arylation of all three C-H bonds and regioselective N-alkylation enabled by SEM-group transposition. J. Org. Chem. 75, 4911-4920 (2010).
30. Shibahara, F., Yamaguchi, E. & Murai, T. Direct arylation of simple azoles catalyzed by 1,10-phenanthroline containing palladium complexes: an investigation of C4 arylation of azoles and the synthesis of triarylated azoles by sequential arylation. J. Org. Chem. 76, 2680-2693 (2011).
31. Yamaguchi, J., Yamaguchi, A. D. & Itami, K. C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals. Angew. Chem. Int. Ed. 51, 8960-9009 (2012).
32. Segawa, Y., Maekawa, T. & Itami, K. Synthesis of extended π-systems through C-H activation. Angew. Chem. Int. Ed. 54, 66-81 (2015).
33. Wencel-Delord, J. & Glorius, F. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules. Nature Chem. 5, 369-375 (2013).
34. Ackermann, L., Vicente, R. & Kapdi, A. Transition-metal-catalyzed direct arylations of (hetero)arenes via C-H bond cleavage. Angew. Chem. Int. Ed. 48, 9792-9826 (2009).
35. Davies, H. M. L. & Manning, J. R. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion. Nature 451, 417-424 (2008).
36. Tang, R-Y., Li, G. & Yu, J-Q. Conformation-induced remote meta-C-H activation of amines. Nature 507, 215-220 (2014).
37. Cheng, C. & Hartwig, J. F. Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol. Science 343, 853-857 (2014).
38. McNally, A., Haffemayer, B., Collins, B. S. L. & Gaunt, M. J. Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles. Nature 510, 129-133 (2014).
39. Fujiwara, Y. et al. Practical and innate carbon-hydrogen functionalization of heterocycles. Nature 492, 95-99 (2012).
40. Chen, M. S. & White, M. C. Combined effects on selectivity in Fe-catalyzed methylene oxidation. Science 327, 566-571 (2010).
41. Ogliaruso, M. A., Romanelli, M. G. & Becker, E. I. Chemistry of cyclopentadienones. Chem. Rev. 65, 261-367 (1965).
42. Saito, S. & Yamamoto, Y. Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives. Chem. Rev. 100, 2901-2916 (2000).
43. Yanagisawa, S., Sudo, T., Noyori, R. & Itami, K. Direct C-H arylation of (hetero) arenes with aryl iodides via rhodium catalysis. J. Am. Chem. Soc. 128, 11748-11749 (2006).
44. Ueda, K., Yanagisawa, S., Yamaguchi, J. & Itami, K. A general catalyst for the β-selective C-H bond arylation of thiophenes with iodoarenes. Angew. Chem. Int. Ed. 49, 8946-8949 (2010).
45. Kirchberg, S. et al. Oxidative biaryl coupling of thiophenes and thiazoles with arylboronic acids through palladium catalysis otherwise difficult C4-selective C-H arylation enabled by boronic acids. Angew. Chem. Int. Ed. 50, 2387-2391 (2011).
46. Thiemann, T. et al. Cycloaddition of thiophene S-oxides to allenes, alkynes and to benzyne. New J. Chem. 27, 1377-1384 (2003).
47. Himeshima, Y., Sonoda, T. & Kobayashi, H. Fluoride-induced 1,2-elimination of o-trimethylsilylphenyl triflate to benzyne under mild conditions. Chem. Lett. 1211-1214 (1983).
48. McKay, C. S., Moran, J. & Pezacki, J. P. Nitrones as dipoles for rapid strainpromoted 1,3-dipolar cycloadditions with cyclooctynes. Chem. Commun. 46, 931-933 (2010).
49. Burke, M. D. & Schreiber, S. L. A planning strategy for diversity-oriented synthesis. Angew. Chem. Int. Ed. 43, 46-58 (2004).
50. Jandeleit, B., Schaefer, D. J., Powers, T. S., Turner, H. W. & Weinberg, W. H. Combinatorial materials science and catalysis. Angew. Chem. Int. Ed. 38, 2494-2532 (1999).