3
040
E. Yagodkin, C. J. Douglas / Tetrahedron Letters 51 (2010) 3037–3040
Y.; Kozlova, L. M.; Klyavinya, Z. P.; Mazheika, I. B.; Gaukhman, A. P. Zhu. Org.
References and notes
Khim. 1985, 21, 2216.
1
0. Suzuki cross-coupling conditions using PEPPSI-IPr, boroxines and additives:
Perkins, J. R.; Carter, R. G. J. Am. Chem. Soc. 2008, 130, 3290.
1. Ru-Phos: (a) Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028; X-
Phos: (b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S.
L. J. Am. Chem. Soc. 2003, 125, 6653.
1
.
Selected reviews and reports on linear acenes as semiconducting materials and
fluorophores: (a) Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296; (b)
Anthony, J. E. Angew. Chem., Int. Ed. 2007, 46, 2; (c) Bendikov, M.; Wudl, F.;
Perepichka, D. F. Chem. Rev. 2004, 104, 4891; (d) Katz, H. E.; Bao, Z.; Gilat, S. L.
Acc. Chem. Res. 2001, 34, 359; (e) Dimitrakopoulos, C. D.; Purushothaman, S.;
Kymissis, J.; Callegari, A.; Shaw, J. M. Science 1999, 283, 822.
1
1
1
1
1
2. Iron catalyzed cross-couplings: Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc.
2007, 129, 9844.
2
3
.
.
Mayumi, U.; Tominari, Y.; Takeya, J. Org. Electron. 2008, 9, 753.
3. Nickel catalyzed cross-coupling conditions adapted from: Saito, S.; Oh-tani, S.;
Miyaura, N. J. Org. Chem. 1997, 62, 8024.
4. Synthesis of 1,2,3,4-tetrachlorotetracene 2a was adapted from: Medne, R. S.;
Livdane, A. D.; Neiland, O. Y. Zhu. Org. Khim. 1975, 13, 624.
5. Hexamethylbenzene is typically synthesized by metal mediated [2+2+2]
reactions of 2-butyne: (a) Ladipo, F. T.; Sarveswaran, V.; Kingston, J. V.;
Huyck, R. A.; Bylikin, S. Y.; Carr, S. D.; Watts, R.; Parkin, S. J. Organomet. Chem.
(a) Gabriel, S.; Leupold, E. Ber. Dtsch. Chem. Ges. 1898, 31, 1159; (b) Moureu, C.;
Dufraisse, C.; Butler, G. L. Acad. Sci., Paris 1926, 183, 101; (c) Moureu, C.;
Dufraisse, C.; Dean, P. M. Acad. Sci., Paris 1926, 182, 1440.
4
.
.
(a) Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001,
123, 9482; (b) Anthony, J. E.; Eaton, D. L.; Parkin, S. R. Org. Lett. 2001, 3, 15; (c)
Rauhut, M. M.; Roberts, B. G.; Mauldin, D. R.; Bergmark, W.; Coleman, R. J. Org.
Chem. 1975, 40, 330; (d) Hanhela, P. J.; Paul, D. B. Aust. J. Chem. 1981, 34, 1710.
Selected reviews on cross-coupling/Kumada–Corriu reactions, reactions with
aryl chlorides: (a) Barnard, C. Platinum Met. Rev. 2008, 52, 38; (b) Kantchev, E. A.
B.; O’Brien, C. J.; Organ, M. M. G. Angew. Chem., Int. Ed. 2007, 46, 2768; (c)
Knochel, P.; Sapountzis, l.; Gommermann, N., 2nd ed.. In Metal-Catalyzed Cross-
Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH, 2004; Vol. 2, p
2
004, 689, 502; (b) Fu, Y.-S.; Yu, S. J. Angew. Chem., Int. Ed. 2001, 40, 437; (c)
Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli, G. J. Organomet. Chem.
000, 607, 57; (d) Choi, K. S.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1998,
9, 1257; (e) Mehnert, C. P.; Chernega, A. N.; Green, M. L. H. J. Organomet. Chem.
996, 513, 247.
5
2
1
1
1
6. For previous syntheses of octamethylnaphthalene, see: (a) Christofi, A. M.;
6
71; (d) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525.
Garratt, P. J.; Hogarth, G.; Ibbett, A. J.; Ng, Y.-F.; Steed, J. W. Tetrahedron 2002,
6
.
.
Yu, Y.; Bond, A. D.; Leonard, P. W.; Lorenz, U. J.; Timofeeva, T. V.; Vollhardt, K. P.
C.; Whitener, G. D.; Yakovenko, A. A. Chem. Commun. 2006, 2572.
Examples of palladium-catalyzed Kumada–Corriu couplings with 2,6-
disubstituted aryl chlorides, (a) four examples, yields range from 18–70%: (a)
Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Hadei, N.; Nasielski, J.; O’Brien, C. J.;
Valente, C. Chem. Eur. J. 2007, 13, 150; two examples, 0–87% yield: (b) Huang, J.;
Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
Palladium-catalyzed Negishi cross-couplings with 2,6-disubstituted aryl
chlorides: Çalimsiz, S.; Sayah, M.; Mallik, D.; Organ, M. G. Angew. Chem., Int.
Ed. 2010, 49, 2014.
5
1
8, 4543; (b) Hart, H.; Lai, C. Y.; Nwokogu, G. C.; Shamouilian, S. Tetrahedron
987, 43, 5203; (c) Hart, H.; Teuerstein, A. Synthesis 1979, 9, 693; (d) Nogina, N.
7
I.; Koptyug, V. A. Zhu. Org. Khim. 1976, 12, 1045.
1
1
7. X-Ray crystallographic structure of octamethylnaphthalene: Sim, G. A. Acta
Cryst. 1982, B38, 623.
8. (a) Itahashi, T.; Kamikawa, T. Cross-Coupling Catalyst Comprising a Cyclic
Nitrogen Ligand and Process Using the Same. Eur. Pat. Appl. 1306131, 2003.;
8
.
.
(
b) Okamoto, K.; Kurita, T.; Sano, A. A Process for Producing 9,10-
Diphenylanthracene. Eur. Pat. Appl. 1132363, 2001.
9. Suzuki–Miyaura coupling of the more electronically activated 9,10-
dichlorooctafluoroanthracene: Tannaci, J. F.; Noji, M.; McBee, J.; Tilley, T. D. J.
Org. Chem. 2007, 72, 5567.
1
9
Synthesis and electronic properties of 5,6,11,12-tetrachlorotetracene 1a: (a)
Yagodkin, E.; Xia, Y.; Kalihari, V.; Frisbie, C. D.; Douglas, C. J. J. Phys. Chem. C.
2
009, 113, 16544; (b) Chi, X.; Li, D.; Zhang, H.; Chen, Y.; Garcia, V.; Garcia, C.;
2
0. Pascal, R. A. Chem. Rev. 2006, 106, 4809.
Siegrist, T. Org. Electron. 2008, 9, 234; (c) Balodis, K. A.; Medne, R. S.; Neiland, O.