-
1
-
-
9644285669
-
-
For original work, see:;;, For reviews on the Sonogashira reactions, see: Angew. Chem., Int. Ed. 2003, 42, 1566-1568
-
For original work, see: Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470 For reviews on the Sonogashira reactions, see: Tykwinski, R. P. Angew. Chem., Int. Ed. 2003, 42, 1566-1568
-
(1975)
Tetrahedron Lett.
, vol.16
, pp. 4467-4470
-
-
Sonogashira, K.1
Tohda, Y.2
Hagihara, N.3
Tykwinski, R.P.4
-
3
-
-
22744442306
-
-
Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 4442-4489
-
-
Nicolaou, K.C.1
Bulger, P.G.2
Sarlah, D.3
-
5
-
-
33846688751
-
-
Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834-871
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 834-871
-
-
Doucet, H.1
Hierso, J.-C.2
-
6
-
-
33751405154
-
-
For bioactive compounds, see
-
For bioactive compounds, see: Boukouvalas, J.; Cote, S.; Ndzi, B. Tetrahedron Lett. 2007, 48, 105-107
-
(2007)
Tetrahedron Lett.
, vol.48
, pp. 105-107
-
-
Boukouvalas, J.1
Cote, S.2
Ndzi, B.3
-
7
-
-
38749133709
-
-
For conjugated functional materials, see; Angew. Chem., Int. Ed. 2007, 46, 8223-8225
-
Falcone, D.; Li, J.; Kale, A.; Jones, G. B. Bioorg. Med. Chem. Lett. 2008, 18, 934-937 For conjugated functional materials, see: Moon, J. H.; McDaniel, W.; MacLean, P.; Hancock, L. F. Angew. Chem., Int. Ed. 2007, 46, 8223-8225
-
(2008)
Bioorg. Med. Chem. Lett.
, vol.18
, pp. 934-937
-
-
Falcone, D.1
Li, J.2
Kale, A.3
Jones, G.B.4
Moon, J.H.5
McDaniel, W.6
MacLean, P.7
Hancock, L.F.8
-
8
-
-
73249138889
-
-
Liu, J.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2009, 109, 5799-5867
-
(2009)
Chem. Rev.
, vol.109
, pp. 5799-5867
-
-
Liu, J.1
Lam, J.W.Y.2
Tang, B.Z.3
-
11
-
-
34447299715
-
-
Kawanami, H.; Matsushima, K.; Sato, M.; Ikushima, Y. Angew. Chem., Int. Ed. 2007, 46, 5129-5132
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 5129-5132
-
-
Kawanami, H.1
Matsushima, K.2
Sato, M.3
Ikushima, Y.4
-
12
-
-
70349481716
-
-
Bakherad, M.; Keivanloo, A.; Bahramian, B.; MIhanparast, S. Tetrahedron Lett. 2009, 50, 6418-6420
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 6418-6420
-
-
Bakherad, M.1
Keivanloo, A.2
Bahramian, B.3
Mihanparast, S.4
-
13
-
-
35748932693
-
-
Biffis, A.; Scattolin, E.; Ravasio, N.; Zaccheria, F. Tetrahedron Lett. 2007, 48, 8761-8764
-
(2007)
Tetrahedron Lett.
, vol.48
, pp. 8761-8764
-
-
Biffis, A.1
Scattolin, E.2
Ravasio, N.3
Zaccheria, F.4
-
14
-
-
70349489979
-
-
Sugimoto, A.; Fukuyama, T.; Rahman, M. T.; Ryu, I. Tetrahedron Lett. 2009, 50, 6364-6367
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 6364-6367
-
-
Sugimoto, A.1
Fukuyama, T.2
Rahman, M.T.3
Ryu, I.4
-
17
-
-
1442301847
-
-
Rathore, R.; Burns, C. L.; Guzei, I. A. J. Org. Chem. 2004, 69, 1524-1530
-
(2004)
J. Org. Chem.
, vol.69
, pp. 1524-1530
-
-
Rathore, R.1
Burns, C.L.2
Guzei, I.A.3
-
18
-
-
0021200442
-
-
Rossi, R.; Carpita, A.; Lezzi, A. Tetrahedron 1984, 40, 2773-2779
-
(1984)
Tetrahedron
, vol.40
, pp. 2773-2779
-
-
Rossi, R.1
Carpita, A.2
Lezzi, A.3
-
19
-
-
0037136485
-
-
Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L.; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A. Org. Lett. 2002, 4, 3199-3202
-
(2002)
Org. Lett.
, vol.4
, pp. 3199-3202
-
-
Mio, M.J.1
Kopel, L.C.2
Braun, J.B.3
Gadzikwa, T.L.4
Hull, K.L.5
Brisbois, R.G.6
Markworth, C.J.7
Grieco, P.A.8
-
20
-
-
53849088070
-
-
Lo., P. K.; Li, K. F.; Wong, M. S.; Cheah, K. W. J. Org. Chem. 2007, 72, 6672-6679
-
(2007)
J. Org. Chem.
, vol.72
, pp. 6672-6679
-
-
Lo, P.K.1
Li, K.F.2
Wong, M.S.3
Cheah, K.W.4
-
21
-
-
38049072099
-
-
Li, G.; Huan, X.; Zhang, L. Angew. Chem., Int. Ed. 2008, 47, 346-349
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 346-349
-
-
Li, G.1
Huan, X.2
Zhang, L.3
-
23
-
-
48049087622
-
-
Csekei, M.; Novak, Z.; Kotschy, A. Tetrahedron 2008, 64, 8992-8996
-
(2008)
Tetrahedron
, vol.64
, pp. 8992-8996
-
-
Csekei, M.1
Novak, Z.2
Kotschy, A.3
-
24
-
-
67449101519
-
-
Nishihara, Y.; Inoue, E.; Ogawa, D.; Okada, Y.; Noyori, S.; Takagi, K. Tetrahedron Lett. 2009, 50, 4643-4646
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 4643-4646
-
-
Nishihara, Y.1
Inoue, E.2
Ogawa, D.3
Okada, Y.4
Noyori, S.5
Takagi, K.6
-
25
-
-
66049132849
-
-
Shi, Y.; Qian, H.; Lucas, N. T.; Xu, W.; Wang, Z. Tetrahedron Lett. 2009, 50, 4110-4113
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 4110-4113
-
-
Shi, Y.1
Qian, H.2
Lucas, N.T.3
Xu, W.4
Wang, Z.5
-
26
-
-
59649096007
-
-
Fang, Z.; Teo, T.-L.; Cai, L.; Lai, Y.-H.; Samoc, A.; Samoc, M. Org. Lett. 2009, 11, 1-4
-
(2009)
Org. Lett.
, vol.11
, pp. 1-4
-
-
Fang, Z.1
Teo, T.-L.2
Cai, L.3
Lai, Y.-H.4
Samoc, A.5
Samoc, M.6
-
27
-
-
0347985383
-
-
Gelman, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2003, 42, 5993-5996
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 5993-5996
-
-
Gelman, D.1
Buchwald, S.L.2
-
28
-
-
13744259806
-
-
Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2005, 46, 1717-1720
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 1717-1720
-
-
Feuerstein, M.1
Doucet, H.2
Santelli, M.3
-
30
-
-
33947202279
-
-
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, 2053-2057
-
(2007)
J. Org. Chem.
, vol.72
, pp. 2053-2057
-
-
Li, J.-H.1
Li, J.-L.2
Wang, D.-P.3
Pi, S.-F.4
Xie, Y.-X.5
Zhang, M.-B.6
Hu, X.-C.7
-
31
-
-
0037174448
-
-
For some selected examples, see
-
For some selected examples, see: Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250-11251
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11250-11251
-
-
Myers, A.G.1
Tanaka, D.2
Mannion, M.R.3
-
32
-
-
0037433513
-
-
Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852-2853
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 2852-2853
-
-
Lalic, G.1
Aloise, A.D.2
Shair, M.D.3
-
33
-
-
4544365674
-
-
Lou, S.; Westbrook, J. A.; Schaus, S. E. J. Am. Chem. Soc. 2004, 126, 11440-11441
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11440-11441
-
-
Lou, S.1
Westbrook, J.A.2
Schaus, S.E.3
-
34
-
-
33746929476
-
-
Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662-664
-
(2006)
Science
, vol.313
, pp. 662-664
-
-
Goossen, L.J.1
Deng, G.2
Levy, L.M.3
-
35
-
-
34247537463
-
-
Goossen, L. J.; Rodríguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824-4833
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 4824-4833
-
-
Goossen, L.J.1
Rodríguez, N.2
Melzer, B.3
Linder, C.4
Deng, G.5
Levy, L.M.6
-
36
-
-
57249105040
-
-
Voutchkova, A.; Coplin, A.; Leadbeater, N. E.; Crabtree, R. H. Chem. Commun. 2008, 6312-6314
-
(2008)
Chem. Commun.
, pp. 6312-6314
-
-
Voutchkova, A.1
Coplin, A.2
Leadbeater, N.E.3
Crabtree, R.H.4
-
37
-
-
52449117955
-
-
Goossen, L. J.; Goossen, K.; Rodríguez, N.; Blanchot, M.; Linder, C.; Zimmermann, B. Pure Appl. Chem. 2008, 80, 1725-1733
-
(2008)
Pure Appl. Chem.
, vol.80
, pp. 1725-1733
-
-
Goossen, L.J.1
Goossen, K.2
Rodríguez, N.3
Blanchot, M.4
Linder, C.5
Zimmermann, B.6
-
39
-
-
57149087486
-
-
Shintani, R.; Park, S.; Shirozu, F.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 16174-16175
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 16174-16175
-
-
Shintani, R.1
Park, S.2
Shirozu, F.3
Murakami, M.4
Hayashi, T.5
-
40
-
-
69949117215
-
-
Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738-5739
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 5738-5739
-
-
Shang, R.1
Fu, Y.2
Li, J.-B.3
Zhang, S.-L.4
Guo, Q.-X.5
Liu, L.6
-
41
-
-
63849187905
-
-
Miyasaki, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M. Chem. - Eur. J. 2009, 15, 3674-3677
-
(2009)
Chem. - Eur. J.
, vol.15
, pp. 3674-3677
-
-
Miyasaki, M.1
Fukushima, A.2
Satoh, T.3
Hirano, K.4
Miura, M.5
-
43
-
-
77950197677
-
-
Xie, K.; Yang, Z.; Zhou, X.; Li, X.; Wang, S.; Tan, Z.; An, X.; Guo, C.-C. Org. Lett. 2010, 12, 1564-1567
-
(2010)
Org. Lett.
, vol.12
, pp. 1564-1567
-
-
Xie, K.1
Yang, Z.2
Zhou, X.3
Li, X.4
Wang, S.5
Tan, Z.6
An, X.7
Guo, C.-C.8
-
44
-
-
77949303400
-
-
Bilodeau, F.; Brochu, M.-C.; Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550-1560
-
(2010)
J. Org. Chem.
, vol.75
, pp. 1550-1560
-
-
Bilodeau, F.1
Brochu, M.-C.2
Guimond, N.3
Thesen, K.H.4
Forgione, P.5
-
45
-
-
76249114336
-
-
Goossen, L. J.; Rodríguez, N.; Lange, P. P.; Linder, C. Angew. Chem., Int. Ed. 2010, 49, 1111-1114
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 1111-1114
-
-
Goossen, L.J.1
Rodríguez, N.2
Lange, P.P.3
Linder, C.4
-
46
-
-
75749132759
-
-
Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 592-595
-
(2010)
Org. Lett.
, vol.12
, pp. 592-595
-
-
Yamashita, M.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
47
-
-
74949121482
-
-
Zhang, S.-L.; Fu, Y.; Shang, R.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2010, 132, 638-646
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 638-646
-
-
Zhang, S.-L.1
Fu, Y.2
Shang, R.3
Guo, Q.-X.4
Liu, L.5
-
50
-
-
74949087531
-
-
Yu, M.; Pan, D.; Jia, W.; Chen, W.; Jiao, N. Tetrahedron Lett. 2010, 51, 1287-1290
-
(2010)
Tetrahedron Lett.
, vol.51
, pp. 1287-1290
-
-
Yu, M.1
Pan, D.2
Jia, W.3
Chen, W.4
Jiao, N.5
-
51
-
-
43549101428
-
-
Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945-948
-
(2008)
Org. Lett.
, vol.10
, pp. 945-948
-
-
Moon, J.1
Jeong, M.2
Nam, H.3
Ju, J.4
Moon, J.H.5
Jung, H.M.6
Lee, S.7
-
52
-
-
64549098217
-
-
Moon, J.; Jang, M.; Lee, S. J. Org. Chem. 2009, 74, 1403-1406
-
(2009)
J. Org. Chem.
, vol.74
, pp. 1403-1406
-
-
Moon, J.1
Jang, M.2
Lee, S.3
-
54
-
-
77956498968
-
-
note
-
We could not identify directly the intermediates 4 and 5 in the reaction mixture by GC and NMR because the two intermediates have acidic protons, which are difficult to detect in the basic conditions. Therefore, we treated the reaction mixture of Table 4 with the following procedure. The reaction mixture was reacted with MeI (1.0 mmol) and DBU (1.0 mmol) at room temperature for 3 h for the conversion of phenylpropiolic acid to methyl phenylpropiolate and treated with HCl etherate (1.0 mmol) for the acidification of phenylacetylene. These two compounds were detected in GC and NMR.
-
-
-
-
55
-
-
77956540710
-
-
note
-
We found similar results when 4-iodotoluene and phenyl bromide were employed as aryl halides instead of phenyl iodide and 4-bromotoluene.
-
-
-
-
57
-
-
33751313526
-
-
Zhang, W.; Wu, H.; Liu, Z.; Zhong, P.; Zhang, L.; Huang, X.; Cheng, J. Chem. Commun. 2006, 46, 4826-4828
-
(2006)
Chem. Commun.
, vol.46
, pp. 4826-4828
-
-
Zhang, W.1
Wu, H.2
Liu, Z.3
Zhong, P.4
Zhang, L.5
Huang, X.6
Cheng, J.7
-
58
-
-
33845522428
-
-
Mino, T.; Shirae, Y.; Saito, T.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2006, 71, 9499-9502
-
(2006)
J. Org. Chem.
, vol.71
, pp. 9499-9502
-
-
Mino, T.1
Shirae, Y.2
Saito, T.3
Sakamoto, M.4
Fujita, T.5
-
60
-
-
33646923980
-
-
Wan, S.; Wang, S. R.; Lu, W. J. J. Org. Chem. 2006, 71, 4349-4352
-
(2006)
J. Org. Chem.
, vol.71
, pp. 4349-4352
-
-
Wan, S.1
Wang, S.R.2
Lu, W.J.3
-
62
-
-
36649015355
-
-
Li, C. W.; Wang, C. I.; Liao, H. Y.; Chaudhuri, R.; Liu, R. S. J. Org. Chem. 2007, 72, 9203-9207
-
(2007)
J. Org. Chem.
, vol.72
, pp. 9203-9207
-
-
Li, C.W.1
Wang, C.I.2
Liao, H.Y.3
Chaudhuri, R.4
Liu, R.S.5
-
63
-
-
34547168951
-
-
Yi, C.; Hua, R.; Zeng, H.; Huang, Q. Adv. Synth. Catal. 2007, 349, 1738-1742
-
(2007)
Adv. Synth. Catal.
, vol.349
, pp. 1738-1742
-
-
Yi, C.1
Hua, R.2
Zeng, H.3
Huang, Q.4
-
64
-
-
51049110773
-
-
Xie, C; Liu, L.; Zhang, Y.; Xu, P. Org. Lett. 2008, 10, 2393-2396
-
(2008)
Org. Lett.
, vol.10
, pp. 2393-2396
-
-
Xie, C.1
Liu, L.2
Zhang, Y.3
Xu, P.4
-
65
-
-
56449112224
-
-
Monnier, F.; Turtaut, F.; Duroure, L.; Taillefer, M. Org. Lett. 2008, 10, 3203-3206
-
(2008)
Org. Lett.
, vol.10
, pp. 3203-3206
-
-
Monnier, F.1
Turtaut, F.2
Duroure, L.3
Taillefer, M.4
-
67
-
-
48249116763
-
-
Huang, H.; Liu, H.; Jiang, H.; Chen, K. J. Org. Chem. 2008, 73, 6037-6040
-
(2008)
J. Org. Chem.
, vol.73
, pp. 6037-6040
-
-
Huang, H.1
Liu, H.2
Jiang, H.3
Chen, K.4
-
68
-
-
56449103061
-
-
Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2008, 73, 9061-9064
-
(2008)
J. Org. Chem.
, vol.73
, pp. 9061-9064
-
-
Huang, H.1
Jiang, H.2
Chen, K.3
Liu, H.4
|