10462
S. Haneda et al. / Tetrahedron 65 (2009) 10459–10462
Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39–46; (g) Kawano, T.;
d 138.3, 136.9, 135.8, 131.2, 128.6, 128.3, 128.2,
(100.6 MHz, CDCl3):
128.1, 126.7, 122.0, 120.8, 119.8, 110.5, 102.5, 17.6.
Shinomaru, T.; Ueda, I. Org. Lett. 2002, 4, 2545–2547; (h) Grasa, G. A.; Singh, R.;
Stevens, E. D.; Nolan, S. P. J. Organomet. Chem. 2003, 687, 269–279; (i) Na´jera, C.;
´
¨
Gil-Molto, J.; Karlstrom, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451–1454; (j) Iyer,
S.; Kulkarni, G. M.; Ramesh, C. Tetrahedron 2004, 60, 2163–2172; (k) Gupta, A.
K.; Song, C. H.; Oh, C. H. Tetrahedron Lett. 2004, 45, 4113–4116; (l) Reddy, K. R.;
Krishna, G. G. Tetrahedron Lett. 2005, 46, 661–663; (m) Cui, X.; Zhou, Y.; Wang,
N.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 163–167.
4.1.14. N-(4-Methylphenyl)-2-phenylindole32. Yield: 38%; Rf¼0.30
(hexane); IR (KBr): vmax (cmꢁ1) 3029, 1500, 1459, 1449, 1324, 1257,
1212, 1134, 793, 742, 710, 692; 1H NMR (400 MHz, CDCl3):
d 7.67 (d,
J¼6.0 Hz, 1H), 7.3–7.1 (m, 12H), 6.78 (s, 1H), 2.38 (s, 3H); 13C NMR
10. Nitrogen monodentate–palladium catalyzed Mizoroki–Heck reactions: (a)
Gossage, R. A.; Jenkins, H. A.; Yadav, P. N. Tetrahedron Lett. 2004, 45, 7689–7691;
(b) Eisnor, C. R.; Gossage, R. A.; Yadav, P. N. Tetrahedron 2006, 62, 3395–3401
and references cited therein.
(100.6 MHz, CDCl3):
d 140.7, 139.1, 137.0, 135.8, 132.6, 129.8, 128.8,
128.2, 128.1, 127.7, 127.2, 122.2, 120.5, 120.4, 110.6, 103.4, 21.1.
11. (a) Klapars, A.; Antila, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123,
7727–7729; (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002,
124, 7421–7428; (c) Antila, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc.
2002, 124, 11684–11688; (d) Antila, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S.
L. J. Org. Chem. 2004, 69, 5578–5587.
12. (a) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581–584; (b) Job,
G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703–3706.
13. (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459–
12467; (b) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583–2586; (c) Ma, D.; Cai, Q.;
Zhang, H. Org. Lett. 2003, 5, 2453–2455; (d) Zhang, H.; Cai, Q.; Ma, D. J. Org.
Chem. 2005, 70, 5164–5173.
14. (a) Zhu, D.; Xu, L.; Wu, F.; Mao, J.; Wan, B. Tetrahedron Lett. 2006, 47, 5781–
5784; (b) Xu, L.; Mao, J.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Tetrahedron 2006, 61,
6553–6560.
15. (a) Cristeau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem.dEur. J. 2004, 10,
5607–5622; (b) Cristeau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org.
Chem. 2004, 695–700; (c) Jiang, Q.; Jiang, D.; Jiang, H.; Fu, H.; Zhao, Y. Synlett
2007, 1836–1842.
16. (a) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742–8743; (b) de
Lange, B.; Lambers-Verstappen, M. H.; de Schmieder-van Vondovoroort, L.;
Sereinig, N.; Rijk, R.; de Vries, A. H. M.; de Vries, J. G. Synlett 2006, 3105–3109;
(c) Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490–
3491; (d) Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 337–339.
17. Other ligands, see: (a) Lu, Z.; Twieg, R. J. Tetrahedron Lett. 2005, 46, 2997–3001;
(b) Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2005, 70, 8107–8109; (c) Zhu,
X.; Ma, Y.; Su, L.; Song, H.; Chen, G.; Liang, D.; Wan, Y. Synthesis 2006, 3955–
3962; (d) Altman, R. A.; Koval, E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190–
6199; (e) Rout, L.; Jammi, S.; Punniyamurthy, T. Org. Lett. 2007, 9, 3397–3399; (f)
Xu, H.; Wolf, C. Chem. Commun. 2009, 1715–1717.
18. For reviews, see: (a) Hassan, J.; Sevignon, M.; Cozzi, C.; Schulz, E.; Lamaire, M.
Chem. Rev. 2002, 102, 1359–1470; (b) Ley, S. V.; Thomas, A. W. Angew. Chem.,
Int. Ed. 2003, 42, 5400–5449; (c) Kunz, K.; Scholz, U.; Ganzer, D. Synlett
2003, 2428–2439; (d) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev.
2004, 248, 2337–2364; (e) Monnier, F.; Tailefer, M. Angew. Chem., Int. Ed.
2008, 47, 3096–3099; (f) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev.
2008, 108, 3054–3131.
4.1.15. 5-(4-Methylphenoxy)-1H-indole (entry 1 in Table 4). Yield:
82%; Rf¼0.68 (hexane:ethyl acetate¼1:1); IR (KBr): vmax (cmꢁ1
)
3019, 1516, 1474, 1454, 1324, 1217, 1212, 1153, 1115, 1070, 788, 753;
1H NMR (400 MHz, CDCl3):
(s, 1H), 6.77 (d, J¼8.0 Hz, 1H), 6.63 (s, 1H), 4.54 (s, 1H), 2.42 (s, 3H);
13C NMR (100.6 MHz, CDCl3):
149.8,137.3,136.2,131.4,130.1,130.0,
d 7.6–7.4 (m, 3H), 7.3–7.2 (m, 3H), 7.07
d
128.8, 124.0, 111.8, 111.3, 105.3, 102.4, 21.0. Anal. Calcd for C15H13NO:
C, 80.69; H, 5.87. Found: C, 80.30; H, 5.92.
4.1.16. N-(4-Methylphenyl)-5-(4-methylphenoxy)indole27 (entry 2 in
Table 4). Yield: 19%; Rf¼0.85 (hexane:ethyl acetate¼1:1); IR (KBr):
vmax (cmꢁ1) 3058, 3032, 1609, 1518, 1470, 1250, 1219, 1167, 756,
736; 1H NMR (400 MHz, CDCl3):
d
7.46 (d, J¼9.2 Hz, 2H), 7.36 (d,
J¼6.0 Hz, 3H), 7.3–7.2 (m, 4H), 7.08 (d, J¼8.8 Hz, 2H), 6.9–6.8 (m,
3H), 7.08 (d, J¼8.8 Hz, 2H), 6.57 (s, 1H), 2.41 (s, 3H), 2.30 (s, 3H);
13C NMR (100.6 MHz, CDCl3):
d 156.7, 150.1, 137.2, 136.4, 132.7,
131.5, 130.1, 130.0, 129.7, 129.0, 124.1, 117.7, 115.5, 1113.3, 110.7,
103.0, 21.0, 20.6.
Acknowledgements
This work was supported by a Grant-in-Aid for Scientific Re-
search on Priority Areas ‘Advanced Molecular Transformations of
Carbon Resources’ and No. B17340020 from the Ministry of Edu-
cation, Culture, Sports, Science and Technology, Japan. S.H. is
grateful to Grant-in-Aid for JSPS Fellows.
Supplementary data
19. Forcopper-catalyzed N-arylation of indoles: (a) 11(c); (b) 13(d); (c) Kantam, M. L.;
Yadav, J.; Laha, S.; Sreedhar, B.; Jha, S. Adv. Synth. Catal. 2007, 349, 1938–1942; (d)
Periasamy, M.; Vairaprakash, P.; Dalai, M. Organometallics 2008, 27, 1963–1966;
(e) Tang, B.-X.; Guo, S.-M.; Zhang, M.-B.; Li, J.-H. Synthesis 2008, 1707–1716.
20. (a) Kawashita, Y.; Nakamichi, N.; Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5,
3713–3716; (b) Hayashi, M. Chem. Rec. 2008, 8, 252–267.
Supplementary data associated with this article can be found in
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