1766
M. Georgy et al. / Tetrahedron 65 (2009) 1758–1766
M. Angew. Chem., Int. Ed. 2006, 45, 4835–4839; (c) Inada, Y.; Nishibayashi, Y.;
4.2.37. 1-(Hept-2-ynyl)-2-methylbenzene (49)
Uemura, S. Angew. Chem., Int. Ed. 2005, 44, 7715–7717.
Prepared with 1.2 equiv of triethylsilane and isolated as a clear
oil.
6. (a) Bustelo, E.; Dixneuf, P. H. Adv. Synth. Catal. 2007, 349, 933–942; (b) Bustelo,
E.; Dixneuf, P. H. Adv. Synth. Catal. 2005, 347, 393–397; (c) Cadierno, V.; Diez, J.;
Garcia-Garrido, S. E.; Gimeno, J. Chem. Commun. 2004, 2716–2717.
7. Luzung, M. R.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 15760–15761.
8. Ohri, R. V.; Radosevich, A. T.; Hrovat, K. J.; Musich, C.; Huang, D.; Holman, T. R.;
Toste, F. D. Org. Lett. 2005, 7, 2501–2504.
1H NMR (CDCl3, 400 MHz)
d
ppm 0.92 (t, 3H, J¼7.2 Hz),1.38–1.55
(m, 4H), 2.22 (tt, J¼2.0, 7.1 Hz, 2H), 2.31 (s, 3H), 3.50 (t, J¼2.3 Hz,
2H), 7.15–7.21 (m, 3H), 7.45 (d, J¼6.9 Hz, 1H); 13C NMR (CDCl3,
9. Sherry, B. D.; Radosevich, A. T.; Toste, F. D. J. Am. Chem. Soc. 2003, 125,
6076–6077.
100 MHz)
d ppm 13.6, 18.5, 19.2, 22.0, 23.3, 31.1, 77.0, 82.8, 126.0,
126.6, 128.1, 130.0, 135.8, 135.9; HREIMS m/z 186.1404, calcd for
10. Kennedy-Smith, J. J.; Young, L. A.; Toste, F. D. Org. Lett. 2004, 6, 1325–1327.
11. Kuninobu, Y.; Ishii, E.; Takai, K. Angew. Chem., Int. Ed. 2007, 46, 3296–
3299.
C14H18 186.1409; IR (film) cmꢀ1 2960, 2931, 2873, 2199, 1707, 1602.
4.2.38. N-Tosyl-1,10-diphenylmethylamine (51)31
Prepared with 3 equiv of tosylamine and isolated as a white
solid.
12. For a preliminary communication, see: Georgy, M.; Boucard, V.; Campagne, J. M.
J. Am. Chem. Soc. 2005, 127, 14180–14181.
13. Liu, J.; Muth, E.; Floerke, U.; Henkel, G.; Merz, K.; Sauvageau, J.; Schwake, E.;
Dyker, G. Adv. Synth. Catal. 2006, 348, 456–462.
14. (a) Sanz, R.; Martinez, A.; Alvarez-Gutierrez, J. M.; Rodriguez, F. Eur. J. Org. Chem.
2006, 1383–1386; (b) Zhan, Z.-P.; Yu, J.-L.; Liu, H.-J.; Cui, Y.-Y.; Yang, R.-F.; Yang,
W.-Z.; Li, J.-P. J. Org. Chem. 2006, 71, 8298–8301.
15. Sanz, R.; Miguel, D.; Martinez, A.; Alvarez-Gutierrez, J. M.; Rodriguez, F. Org.
Lett. 2007, 9, 727–730.
1H NMR (CDCl3, 300 MHz)
d
ppm 2.38 (s, 3H), 5.24 (d, J¼7.1 Hz,
1H), 5.58 (d, J¼7.1 Hz, 1H), 7.09–7.23 (m, 12H), 7.57 (d, J¼8.3 Hz,
2H); 13C NMR (CDCl3, 75 MHz)
ppm 21.4, 61.3, 127.2 (2C), 127.3
d
(4C), 127.5 (2C), 128.5 (4C), 129.3 (2C), 137.3, 140.5 (2C), 143.2. Data
are in accordance with previously reported results.31
16. Sanz, R.; Martinez, A.; Miguel, D.; Alvarez-Gutierrez, J. M.; Rodriguez, F.
Synthesis 2007, 3252–3256.
17. Huang, W.; Shen, Q.; Wang, J.; Zhou, X. J. Org. Chem. 2008, 73, 1586–1589.
18. (a) Yadav, J. S.; Reddy, B. V. S.; Rao, T. S.; Rao, K. V. R. Tetrahedron Lett. 2008, 49,
614–618; (b) Hui, H.-h.; Zhao, Q.; Yang, M.-y.; She, D.-b.; Chen, M.; Huang, G.-s.
Synthesis 2008, 191–196; (c) Lee, K.; Lee, P. H. Org. Lett. 2008, 10, 2441–2444; (d)
Yadav, J. S.; Reddy, B. V. S.; Rao, K. V. R.; Kumar, G. G. K. S. N. Synthesis 2007,
3205–3210; (e) Zhan, Z.-P.; Yang, W.-Z.; Yang, R.-F.; Yu, J.-L.; Li, J.-P.; Liu, H.-J.
Chem. Commun. 2006, 3352–3354; (f) Qin, H.; Yamagiwa, N.; Matsunaga, S.;
Shibasaki, M. Angew. Chem., Int. Ed. 2007, 46, 409–413; (g) Yadav, J. S.; Reddy, B.
V. S.; Rao, K. V. R.; Kumar, G. G. K. S. N. Tetrahedron Lett. 2007, 48, 5573–5576;
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(i) Srihari, P.; Reddy, J. S. S.; Bhunia, D. C.; Mandal, S. S.; Yadav, J. S. Synth.
Commun. 2008, 38, 1448–1455; (j) Srihari, P.; Bhunia, D. C.; Sreedhar, P.;
Mandal, S. S.; Reddy, J. S. S.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 8120–8124.
19. Kabalka, G. W.; Yao, M.-L. Curr. Org. Synth. 2008, 5, 28–32.
20. (a) Kabalka, G. W.; Yao, M.-L.; Borella, S. J. Am. Chem. Soc. 2006, 128, 11320–
11321; (b) Kabalka, G. W.; Wu, Z.; Ju, Y. Org. Lett. 2004, 6, 3929–3931.
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refs. cited.
4.2.39. N-Tosyl-1-phenylethylamine (53)31
Prepared with 3 equiv of tosylamine and isolated as a white
solid.
1H NMR (CDCl3, 300 MHz)
d
ppm 1.42 (d, J¼6.9 Hz, 3H), 2.39 (s,
3H), 4.47 (quint, J¼6.9 Hz, 1H), 5.23 (d, J¼7.1 Hz, 1H), 7.10–7.13 (m,
2H), 7.16–7.19 (m, 5H), 7.63 (d, J¼8.1 Hz, 2H); 13C NMR (CDCl3,
75 MHz)
d ppm 21.4, 23.5, 53.6, 126.1 (2C), 127.0 (2C), 127.3, 128.4
(2C), 129.4 (2C), 137.6, 142.0, 143.0. Data are in accordance with
previously reported results.31
4.2.40. N-(1,3-Diphenyl-2(E)-propenyl)-4-methyl-
benzenesulfonamide (55)43
Prepared with 1.1 equiv of tosylamine and isolated as a white
solid.
22. Lu, G.; Li, Y.-M.; Li, X.-S.; Chan, A. S. C. Coord. Chem. Rev. 2005, 249, 1736–1744.
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3560–3578.
25. Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126,
10858–10859.
1H NMR (CDCl3, 400 MHz)
d
ppm 2.16 (s, 3H), 4.97 (dd, J¼6.7,
6.9 Hz, 1H), 5.38 (d, J¼7.5 Hz, 1H), 5.93 (dd, J¼6.8, 15.8 Hz, 1H), 6.19
(d, J¼15.7 Hz,1H), 6.96–7.13 (m,12H), 7.52 (m, 2H); 13C NMR (CDCl3,
100 MHz)
d ppm 21.3, 59.7, 126.5 (2C), 127.0 (2C), 127.2 (2C), 127.7,
26. Michelet, V.; Toullec, P. Y.; Geneˆt, J.-P. Angew. Chem., Int. Ed. 2008, 47,
4268–4315.
127.8, 128.1, 128.4 (2C), 128.6 (2C), 129.4 (2C), 131.9, 136.0, 137.6,
139.6, 143.2. Data are in accordance with previously reported
results.43
27. Debleds, O.; Campagne, J.-M. J. Am. Chem. Soc. 2008, 130,
1562–1563.
28. The low yield observed in the formation of 26 is mainly due to the instability of
the compound, which rapidly decomposes at rt.
29. For recent accounts dealing with gold-catalyzed Meyer–Schuster rearrange-
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D. B. Tetrahedron 1984, 40, 1371–1380.
Acknowledgements
We are grateful to the CNRS for financial support (ATIPE jeune
´
equipe), the Institut de Chime des Substances Naturelles (Gif-sur-
Yvette) and MENRT for Ph.D. grants (OD, CDZ, MG). We also thank
Prof. Damien Prim for helpful discussions.
31. Terrasson, V.; Marque, S.; Georgy, M.; Campagne, J.-M.; Prim, D. Adv. Synth.
Catal. 2006, 348, 2063–2067.
32. For related Au-catalyzed substitutions on benzylic positions, see: (a) Ref. 13; (b)
Mertins, K.; Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2006, 348,
691–695.
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