Sonogashira Cross-Coupling Catalysed by Cu-Free Pd Zeolites
FULL PAPERS
C6H4[], 7.32 [d, 3J(H,H)¼8.0 Hz, 2H, o-CH3-C6H4], 5.93
[7] T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, I. Ryu,
Org. Lett. 2002, 4, 1691.
[8] a) T. Okita, M. Isobe, Synlett 1994, 589; b) J.-F. Nguefack,
V. Bolitt, D. Sinou, Tetrahedron Lett. 1996, 37, 5527; c) T.
Hundertmark, A. F. Littke, S. L. Buchwald, G. C. Fu,
Org. Lett. 2000, 2, 1729; d) M. R. Netherton, G. C. Fu,
4
¼
[pseudo-q, J(H,H)¼1.5 Hz, 1H, CH3-C(O) CH-C(OSO2)],
4
¼
5.74 [d, J(H,H)¼1.8 Hz, 1H, O-C(O)-CH C(OSO2)], 2.41
(s, 3H, C6H4-CH3), 2.17 [s, 3H, CH C(O)-CH3]; 13C NMR
¼
¼
(62.9 MHz, CDCl3): d¼162.27 (SO2-O-C CH), 160.82
¼
¼
(C O), 159.94 (CH3C CH), 144.72 (Cq-SO2, C6H4), 129.58
(Cq-CH3, C6H4), 128.28 (o-CH3, C6H4), 126.35 (o-SO2, C6H4),
´
´
G. C. Org. Lett. 2001, 3, 4295; e) D. Mery, K. Heuze, D.
Astruc, Chem. Commun. 2003, 1934; f) N. E. Leadbeater,
B. J. Bonnie, Tetrahedron Lett. 2003, 44, 8653; g) A. So-
heili, J. Albaneze-Walker, J. A. Murry, P. G. Dormer,
D. L. Hughes, Organic Lett. 2003, 5, 4191; h) Y. Uozumi,
Y. Kobayashi, Heterocycles 2003, 59, 71; i) L. Djakovitch,
¼
98.71[CH -C CH-C(OSO2)], 98.60 [O-C(O)-CH-C(OSO2)],
3
¼
19.79 (C6H4-CH3), 18.16 [CH C(O)-CH3]; C13H12O5S: mol.
wt.: 280.29 g·molꢀ1; MS: m/z (%)¼[Mþ] 280 (4), [C7H7O2Sþ]
155 (47), [C5H4O2Sþ] 132 (32), [C7H7þ] 91(100).
`
P. Rollet, Tetrahedron Lett. 2004, 45, 1367; j) A. Arques,
˜
D. Aunon, P. Molina, Tetrahedron Lett. 2004, 45, 4337.
References
[9] a) N. A. Powell, S. D. Rychnosky, Tetrahedron Lett. 1996,
37, 7901; b) G. T. Crisp, P. D. Turner, K. A. Stephens, J.
Organomet. Chem. 1998, 570, 219; c) K. Nakamura, H.
Ohubo, M. Yamaguchi, Synlett 1999, 549; d) W.-M. Dai,
D.-S. Guo, L.-P. Sun, Tetrahedron Lett. 2001, 42, 5275.
[10] I. P. Beletskaya, G. V. Latyshev, A. V. Tsvetkov, N. V. Lu-
kashev, Tetrahedron Lett. 2003, 44, 5011.
[11] L. Wang, L. Pinhua, Y. Zhang, Chem. Commun. 2004,
514.
[12] N. E. Leadbeater, M. Marco, B. J. Tominack, Organic
Lett. 2003, 5, 3919.
[13] P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem.
Int. Ed. 2000, 39, 2632.
[14] J.-P. Genet, E. Blart, M. Savignac, Synlett 1992, 715.
[15] M. Alami, F. Ferri, G. Linstrumelle, Tetrahedron Lett.
1993, 34, 6403.
[16] V. P. Bçhm, W. A. Herrmann, Eur. J. Org. Chem. 2000,
3679.
[1] a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402 and referen-
ces cited therein; b) T. Hiyama, in: Metal-Catalyzed
Cross-Coupling Reactions, (Eds.: F. Diederich, P. J.
Stang), Wiley-VCH Weinheim, 1998, Chapter 10 and ref-
erences cited therein; c) K. Sonogashira, J. Organomet.
Chem. 2002, 653, 46; d) K. Sonogashira, in: Handbook
of Organopalladium Chemistry for Organic Synthesis,
(Ed.: E. Negishi), Wiley-VCH, New York, 2002;
e) R. R. Tykwinski, Angew Chem. Int. Ed. Engl. 2003,
42, 1566; f) E.-I. Negishi, L. Anastasia, Chem. Rev.
2003, 103, 1979.
[2] a) Modern Acetylene Chemistry, (Eds.: P. J. Stang, F. Die-
derich), VCH, Weinheim, 1995; b) Modern Arene Chem-
istry, (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002.
[3] a) L. Brandsma, S. F. Vasilevsky, H. D. Verkruijsse, Ap-
plications of Transition Metal Catalysts in Organic Syn-
thesis, Springer, Berlin, 1988, Chap. 10, pp. 179–225;
b) K. C. Nicolaou, E. J. Sorensen, Classics in Total Syn-
thesis, Wiley-VCH, Weinheim, 1996, p. 582; c) A. E. Gra-
ham, D. McKerrecher, D. H. Davies, R. J. K. Taylor, Tet-
rahedron Lett. 1996, 37, 7445; d) M. W. Miller, C. R.
Johnson, J. Org. Chem. 1997, 62, 1582; e) A. Sakai, T.
Aoyama, T. Shioiri, Tetrahedron Lett. 1999, 40, 4211;
f) F. Yoshimura, S. Kawata, M. Hirama, Tetrahedron
Lett. 1999, 40, 8281; g) M. Toyota, C. Komori, M. Ihara,
J. Org. Chem. 2000, 65, 7110; h) I. Paterson, R. D. M. Da-
vies, R. Marquez, Angew. Chem. Int. Ed. 2001, 40, 603;
i) J.-i. Uenishi, K. Matsui, H. Ohmiya, J. Organomet.
Chem. 2002, 653, 141.
[4] K. Sonogashira, in: Comprehensive Organic Synthesis,
Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon Press,
New York, 1991, pp. 521–549.
[5] H.-F. Chow, C.-W. Wan, K.-H. Low, Y.-Y Yeung,. J. Org.
Chem. 2001, 66, 1 91 0.
[6] a) A. L. Casalnuovo, J. C. Calabrese, J. Am. Chem. Soc.
1990, 112, 4324; b) H. Dibowski, F. P. Schmidtchen, Tet-
rahedron Lett. 1998, 39, 525; c) G. W. Kabalka, L.
Wang, V. Namboodiri, R. M. Pagni, Tetrahedron Lett.
2000, 41, 5151; d) D. T. Bong, M. R. Ghadiri, Org. Lett.
2001, 3, 2509; e) M. J. Mio, L. C. Kopel, J. B. Braun,
T. L. Gadzikwa, K. L. Hull, R. G. Brisbois, C. J. Mark-
worth, P. A. Grieco, Org. Lett. 2002, 4, 3199; f) H. Re-
mmele, A. Kçllhofer, H. Plenio, Organometallics 2003,
22, 4098.
ˆ
[17] M. Pal, K. Parasuraman, S. Gupta, K. R. Yeleswarapu,
Synlett 2002, 1976.
[18] X. Fu, S. Zhang, Y. Yin, D. Schumacher, Tetrahedron
Lett. 2002, 43, 6673.
´
[19] a) D. A. Alonso, C. Najera, M. C. Pacheco, Tetrahedron
´
Lett. 2002, 43, 9365; b) D. A. Alonso, C. Najera, M. C.
Pacheco, Adv. Synth. Catal. 2003, 345, 1146.
[20] N. Sakai, K. Annaka, T. Konakahara, Organic Lett. 2004,
6, 1527.
[21] K. Heuze, D. Mery, D. Gauss, D. Astruc, Chem. Com-
mun. 2003, 2274.
[22] R. G. Heidenreich, K. Kçhler, J. G. E. Krauter, J. Pietsch,
Synlett 2002, 1118.
[23] Z. Novak, A. Szabo, J. Repasi, A. Kotschy, J. Org. Chem.
´
´
´
´
´ ´
2003, 68, 3327.
[24] a) L. Djakovitch, K. Kçhler, J. Mol. Catal. A: Chem. 1999,
142, 275; b) L. Djakovitch, H. Heise, K. Kçhler, J. Orga-
nomet. Chem. 1999, 584, 16; c) L. Djakovitch, K. Kçhler,
J. Am. Chem. Soc. 2001, 123, 5990.
[25] a) J. Michalik, M. Narayana, L. Kevan, J. Phys. Chem.
1985, 89, 4553; b) W. M. H. Sachtler, F. A. P. Cacalcanti,
Catal. Lett. 1991, 9, 261.
[26] A. Streitwieser, C. K. Heathcock, E. M. Kosower, Intro-
duction to Organic Chemistry, 4th edn., MacMillan Press,
London, 1992.
[27] W.-M. Dai, K. W. Lai, Tetrahedron Lett. 2002, 43, 9377.
Adv. Synth. Catal. 2004, 346, 1782–1792
asc.wiley-vch.de
ꢀ 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1791