X. Wang et al. / Tetrahedron Letters 50 (2009) 6293–6297
6297
Commun. 2008, 4968; (f) Yang, F.; Cui, X.; Li, Y.; Zhang, J.; Ren, G.; Wu, Y.
Tetrahedron 2007, 63, 1963; (g) Yi, C.; Hua, R. J. Org. Chem. 2006, 71, 2535; (h)
Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2006, 71, 379; (i) Shirakawa, E.;
Kitabata, T.; Otsuka, H.; Tsuchimoto, T. Tetrahedron 2005, 61, 9878; (j) Cheng, J.;
Sun, Y.; Wang, F.; Guo, M.; Xu, J.-H.; Pan, Y.; Zhang, Z. J. Org. Chem. 2004, 69,
5428; (k) Arques, A.; Aunon, D.; Molina, P. Tetrahedron Lett. 2004, 45, 4337; (l)
Gelman, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2003, 42, 5993; (m) Alonso, D.
A.; Nájere, C.; Pacheco, M. C. Tetrahedron Lett. 2002, 43, 9365.
Financial support was also provided by the Special Research Found
from Hokuriku University. All of them are gratefully
acknowledged.
References and notes
1. (a) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874; (b) Doucet, H.; Hierso, J.-
C. Angew. Chem., Int. Ed. 2007, 46, 834; (c) Negishi, E.; Anastasia, L. Chem. Rev.
2003, 103, 1979; (d) Sonogashira, K.. In Handbook of Organopalladium Chemistry
for Organic Synthesis; Negishi, E., Ed.; Wiley Interscience: New York, 2002; Vol.
1, p 493.
2. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467; (b)
Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
3. For selected papers on the palladium-catalyzed homo-coupling reaction of
alkynes, see: (a) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int.
Ed. 2000, 39, 2632; (b) Batsanov, A. S.; Collings, J. C.; Fairlamb, I. S.; Holland, J.
P.; Howard, J. A. K.; Lin, Z.; Marder, T. B.; Parsons, A. C.; Ward, R. M.; Zhu, J. J.
Org. Chem. 2005, 70, 703; (c) Li, J.-H.; Liang, Y.; Zhang, X.-D. Tetrahedron 2005,
61, 1903.
6. Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Angew. Chem., Int. Ed. 2005, 44,
6166.
7. (a) Moiseev, D. V.; Morugova, V. A.; Gushchin, A. V.; Shavirin, A. S.; Kursky, Y.
A.; Dodonov, V. A. J. Organomet. Chem. 2004, 689, 731; (b) Moiseev, D. V.;
Gushchin, A. V.; Shavirin, A. S.; Kursky, Y. A.; Dodonov, V. A. J. Organomet. Chem.
2003, 667, 176; (c) Gushchin, A. V.; Moiseev, D. V.; Dodonov, V. A. Russ. Chem.
Bull., Int. Ed. 2001, 50, 1291; (d) Kang, S.-K.; Ryu, H.-C.; Hong, Y.-T. J. Chem. Soc.,
Perkin Trans. 1 2000, 3350.
8. Kang, S.-. K.; Ryu, H.-C.; Lee, S.-W. J. Organomet. Chem. 2000, 610, 38.
9. Kang, S.-K.; Ryu, H.-C.; Hong, Y.-T. J. Chem. Soc., Perkin Trans. 1 2001, 736.
10. (a) Qin, W.; Yasuike, S.; Kakusawa, N.; Sugawara, Y.; Kawahata, M.; Yamagichi,
K.; Kurita, J. J. Organomet. Chem. 2008, 693, 109; (b) Yasuike, S.; Qin, W.;
Sugawara, Y.; Kurita, J. Tetrahedron Lett. 2007, 48, 721.
4. For selected recent reports on palladium-catalyzed Sonogashira cross-coupling
reactions under Cu-free conditions, see: (a) Zhang, B.-S.; Wang, C.; Gong, J.-F.;
Song, M.-P. J. Organomet. Chem. 2009, 674, 2555; (b) Bakherad, M.; Keivanloo,
A.; Bahramian, B.; Hashemi, M. Tetrahedron Lett. 2009, 50, 1557; (c) Komáromi,
A. K.; Tolnai, G. L.; Novác, Z. Tetrahedron Lett. 2008, 49, 7294; (d) Ljungdahl, T.;
Bennur, T.; Dallas, A.; Emtenäs, H.; Mårtensson, J. Organometallics 2008, 27,
2490; (e) Kim, J.-H.; Lee, D.-H.; Jun, B.-H.; Lee, Y.-S. Tetrahedron Lett. 2007, 48,
7079; (f) Shi, S.; Zhang, Y. Synlett 2007, 1843; (g) Gholap, A. R.; Venkatesan, K.;
Pasricha, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2005, 70,
4869; (h) Li, J.-H.; Liang, Y.; Xie, Y.-X. J. Org. Chem. 2005, 70, 4393; (i) Liang, B.;
Dai, M.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 391; (j) Soheili, A.; Albaneze-
Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191; (k)
Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934; (l) Leadbeater, N. E.;
Tominack, B. J. Tetrahedron Lett. 2003, 44, 8653; (m) Fukuyama, T.; Shinmen,
M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691.
11. (a) Moiseev, D. V.; Morugova, V. A.; Gushchin, A. V.; Dodonov, V. A. Tetrahedron
Lett. 2003, 44, 3155; (b) Matoba, K.; Motofusa, S.; Cho, C. S.; Ohe, K.; Uemura, S.
J. Organomet. Chem. 1999, 574, 3.
12. Triarylantimony diacetates 1a–h were prepared according to the reported
procedure.10a Compound 1c: 50% yield, mp 280À283 °C; 1g: 63% yield, mp
177À182 °C.
13. Typical experiment:
terminal alkynes
a solution of triarylantimony diacetate 1 (0.5 mmol),
(1.25 mmol), and PdCl2(PPh3)2 (0.005 mmol) in 1,4-
2
dioxane (3 mL) was heated at 80 °C for 18 h under air. After dilution with
ether (20 mL) and water (20 mL), the reaction mixture was separated and the
aqueous layer was extracted with ether (20 mL). The combined organic layer
was washed with water, dried over anhydrous MgSO4 and concentrated under
reduced pressure. The crude residue was purified by short column
chromatography on silica gel to give the corresponding diarylacetylene
derivatives 3 and 5–19.
5. For selected recent reports on palladium-catalyzed Sonogashira cross-coupling
reactions under Cu- and amine-free conditions, see: (a) Bolliger, J. L.; Frech, C.
M. Adv. Synth. Catal. 2009, 351, 891; (b) Dash, C.; Shaikh, M.; Ghosh, P. Eur. J.
Inorg. Chem. 2009, 1608; (c) Mori, S.; Yanase, T.; Aoyagi, S.; Monguchi, Y.;
Maegawa, T.; Sajiki, H. Chem. Eur. J. 2008, 14, 6994; (d) Fleckenstein, C. A.;
Plenio, H. Green Chem. 2008, 10, 563; (e) Komároni, A.; Novák, Z. Chem.
14. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400; (b) Lakmini, H.; Ciofini, I.;
Jutand, A.; Amatore, C.; Adamo, C. J. Phys. Chem. A 2008, 112, 12896; (c) Adamo,
C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128,
6829; (d) Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126,
10212.