4806
S. Wang et al. / Tetrahedron 67 (2011) 4800e4806
1979, 866e867; (j) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20,
3H); 13C NMR (100 MHz, CDCl3):
133.04, 122.84, 120.65, 114.42, 113.96, 92.65, 84.61, 55.13.
d
159.88, 151.95, 148.06, 138.04,
3437e3440.
5. Li, J.-H.; Li, J.-L.; Wang, D.-P.; Pi, S.-F.; Xie, Y.-X.; Zhang, M.-B.; Hu, X.-C. J. Org.
Chem. 2007, 72, 2053e2057.
4.3.24. 1-(4-Methoxylphenyl)-1-hexyne26 1H NMR (400 MHz,
.
6. (a) Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Catal. 2010, 352, 458e462; (b)
Pan, C.; Luo, F.; Wang, W.; Ye, Z.; Cheng, J. Tetrahedron Lett. 2009, 50,
5044e5046; (c) Mao, J.; Wu, M.; Guo, J.; Ji, S. Eur. J. Org. Chem. 2008,
4050e4054; (d) Mao, J.; Guo, J.; Ji, S. J. Mol. Catal. A: Chem. 2008, 284, 85e88.
7. (a) He, A.; Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524e2525; (b) Saito, B.; Fu, G. C.
J.Am. Chem. Soc. 2008,130, 6694e6695; (c) Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2007,
129, 9602e9603; (d) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44,
674e688; (e) Netherton, M. R.; Fu, G. C. In Topics in Organometallic Chemistry:
Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: New York, NY, 2005; (f)
Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176e4211; (g) Molander, G.
A.; Biolatto, B. Org. Lett. 2002, 4, 1867e1870; (h) Netherton, M. R.; Dai, C.;
CDCl3): 7.32 (d, J¼8.8 Hz, 2H), 6.80 (d, J¼8.8 Hz, 2H), 3.78 (s, 3H),
d
2.38 (t, J¼7.2 Hz, 2H), 1.59e1.54 (m, 2H), 1.50e1.44 (m, 2H), 0.94 (t,
J¼7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3):
d 158.92, 132.80, 116.22,
113.73, 88.69, 80.18, 55.17, 30.93, 21.99, 19.06, 13.62.
4.3.25. 1-(4-Methoxylphenyl)-1-octyne15
CDCl3):
.
1H NMR (400 MHz,
7.32 (d, J¼8.8 Hz, 2H), 6.81 (d, J¼8.8 Hz, 2H), 3.79 (s, 3H),
d
2.38 (t, J¼7.6 Hz, 2H), 1.61e1.55 (m, 2H), 1.48e1.43 (m, 2H),
€
Neuschutz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099e10100; (i) Wolfe, J. P.;
1.33e1.31 (m, 4H), 0.90 (t, J¼6.8 Hz, 3H); 13C NMR (100 MHz,
Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc.1999,121, 9550e9551; (j)
Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387e3388.
CDCl3):
d 158.95, 132.83, 116.28, 113.78, 88.80, 80.20, 55.23, 31.38,
8. (a) Shi, Y.; Li, X.; Liu, J.; Jiang, W.; Sun, L. Tetrahedron Lett. 2010, 51, 3626e3628;
(b) Yang, X.; Zhu, L.; Zhou, Y.; Li, Z.; Zhai, H. Synthesis 2008, 1729e1732.
9. (a) Yan, J.; Wang, L. Synthesis 2010, 447e452; (b) Wang, M.; Li, P.; Wang, L. Eur. J.
Org. Chem. 2008, 2255e2261; (c) Li, P.; Wang, L.; Zhang, Y. Tetrahedron 2008, 64,
10825e10830; (d) Miao, T.; Wang, L. Tetrahedron Lett. 2007, 48, 95e99; (e)
Wang, L.; Wang, M.; Huang, F. Synlett 2005, 2007e2010.
28.84, 28.61, 22.56, 19.41, 14.05.
Acknowledgements
10. (a) Wang, Y.; Xu, L.; Ma, D. Chem.dAsian J. 2010, 5, 74e76; (b) Maiti, D.; Buchwald,
S. L. J. Am. Chem. Soc. 2009, 131, 17423e17424; (c) Strieter, E. R.; Bhayana, B.;
Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78e79; (d) Chen, Y.; Wang, Y.; Sun, Z.;
Ma, D. Org. Lett. 2008, 10, 625e628; (e) Altman, R. A.; Hyde, A. M.; Huang, X.;
Buchwald, S. L. J. Am. Chem. Soc. 2008,130, 9613e9614; (f) Ma, D.; Cai, Q. Acc. Chem.
Res. 2008, 41, 1450e1460; (g) Martin, R.; Rodriguez Rivero, M.; Buchwald, S. L.
Angew. Chem., Int. Ed. 2006, 45, 7079e7082; (h) Strieter, E. R.; Blackmond, D. I.;
Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120e4121; (i) Ma, D.; Liu, F. Chem.
Commun. 2004, 1934e1935.
11. (a) Molander, G. A.; Canturk, B.; Kennedy, L. E. J. Org. Chem. 2009, 74, 973e980;
(b) Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275e286; (c) Molander, G.
A.; Ribagorda, M. J. Am. Chem. Soc. 2003, 125, 11148e11149; (d) Barder, T. E.;
Buchwald, S. L. Org. Lett. 2004, 6, 2649e2652; (e) Kabalka, G. W.; Venkataiah, B.;
Dong, G. Org. Lett. 2003, 5, 3803e3805; (f) Thadani, A. N.; Batey, R. A. Org. Lett.
2002, 4, 3827e3830; (g) Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4,
107e109.
We gratefully acknowledge the financial support by the National
Natural Science Foundation of China (No. 20972057).
Supplementary data
Supplementary data associated with this article can be found in
References and notes
1. (a) Metal-catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich,
F., Eds.; Wiley-VCH: Weinheim, 2004; (b) Handbook of Organopalladium
Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley-Interscience: New
York, NY, 2002; (c) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed.
2005, 44, 4442e4489.
2. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457e2483; (b) Suzuki, A.
J. Organomet. Chem. 1999, 576, 147e168; (c) Moreno-Manas, M.; Pleixats, R. Acc.
Chem. Res. 2003, 36, 638e643; (d) Suzuki, A. Chem. Commun. 2005, 4759e4763;
(e) Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133e173.
12. (a) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5660e5667; (b) Lu, G.;
ꢀ
Franzen, R.; Zhang, Q.; Xu, Y. Tetrahedron Lett. 2005, 46, 4255e4259; (c) Ville-
€
min, D.; Gomez-Escalonilla, M. J.; Saint-Clair, J. F. Tetrahedron Lett. 2001, 42,
635e637.
13. (a) Maurer, S.; Liu, W.; Zhang, X.; Jiang, Y.; Ma, D. Synlett 2010, 976e978; (b)
Niu, J.; Guo, P.; Kang, J.; Li, Z.; Xu, J.; Hu, S. J. Org. Chem. 2009, 74, 5075e5078;
(c) Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem.
2005, 70, 10135e10138.
14. (a) Hay, A. S. J. Org. Chem. 1960, 25, 1275e1276; (b) Hay, A. S. J. Org. Chem. 1962,
27, 3320e3321; (c) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int.
Ed. 2000, 39, 2632e2657 and references cited therein.
15. Huang, H.; Liu, H.; Jiang, H.; Chen, K. J. Org. Chem. 2008, 73, 6037e6040.
16. Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett.
2008, 10, 945e948.
17. Carril, M.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 4862e4865.
18. Fabrizi, G.; Goggiamani, A.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2010,
49, 4067e4070.
3. (a) Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45,
1282e1284; (b) Kertesz, M.; Choi, C. H.; Yang, S. Chem. Rev. 2005, 105,
3448e3481; (c) Lightowler, S.; Hird, M. Chem. Mater. 2005, 17, 5538e5549; (d)
Albaneze-Walker, J.; Murry, J. A.; Soheili, A.; Ceglia, S.; Springfield, S. A.; Bazaral,
C.; Dormer, P. G.; Hughes, D. L. Tetrahedron 2005, 61, 6330e6336; (e) Wong, K.
T.; Hung, T. S.; Lin, Y.; Wu, C. C.; Lee, G. H.; Peng, S. M.; Chou, C. H.; Su, Y. O. Org.
Lett. 2002, 4, 513e516; (f) Baudoin, O.; Cesario, M.; Guenard, D.; Gueritte, F.
J. Org. Chem. 2002, 67, 1199e1207; (g) Chemler, S. R.; Trauner, D.; Danishefsky,
S. J. Angew. Chem., Int. Ed. 2001, 40, 4544e4568; (h) Nicolaou, K. C.; Boddy, C. N.
€
C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096e2152; (i) The
19. Ito, S.; Nishide, K.; Yoshifuji, M. Organometallics 2006, 25, 1424e1430.
20. Zhang, W. W.; Zhang, X. G.; Li, J. H. J. Org. Chem. 2010, 75, 5259e5264.
21. Yue, D.-W.; Yao, T.-L.; Larock, R. C. J. Org. Chem. 2005, 70, 10292e10296.
22. Tang, B.-X.; Wang, F.; Li, J.-H.; Xie, Y.-X.; Zhang, M.-B. J. Org. Chem. 2007, 72,
6294e6297.
23. Wang, L.; Li, P.-H.; Zhang, Y.-C. Chem. Commun. 2004, 514e515.
24. He, H.; Wu, Y.-J. Tetrahedron Lett. 2004, 45, 3237e3239.
25. Kabalka, G. W.; Al-Masum, M.; Mereddy, A. R.; Dadush, E. Tetrahedron Lett.
2006, 47, 1133e1136.
Chemistry of Natural Products; Thomson, R. H., Ed.; Blackie and Son: Glasgow,
1985.
4. (a) Jin, M.-J.; Lee, D.-H. Angew. Chem., Int. Ed. 2010, 49, 1119e1122; (b) Bolliger, J. L.;
Frech, C. M. Chem.dEur. J. 2010, 16, 4075e4081; (c) Ackermann, L.; Potukuchi, H.
K.; Althammer, A.; Born, R.; Mayer, P. Org. Lett. 2010, 12,1004e1007; (d) Rudolph,
A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656e2670; (e) Sawai, K.; Tatumi,
R.; Nakahodo, T.; Fujihara, H. Angew. Chem., Int. Ed. 2008, 47, 6917e6919; (f)
Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41,1461e1473; (g) Zhou, J.-R.; Fu,
G. C. J. Am. Chem. Soc. 2004, 126, 1340e1341; (h) Miura, M. Angew. Chem., Int. Ed.
2004, 43, 2201e2203; (i) Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun.
26. Lu, B.; Li, C.-Q.; Zhang, L.-M. J. Am. Chem. Soc. 2010, 132, 14070e14072.