-
1
-
-
34250655628
-
-
For recent reviews, see: a, published online
-
For recent reviews, see: (a) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev., published online, 2007, http://dx.doi.org/10.1039/b606984n.
-
(2007)
Chem. Soc. Rev
-
-
Seregin, I.V.1
Gevorgyan, V.2
-
2
-
-
33846918696
-
-
(b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
-
(2007)
Chem. Rev
, vol.107
, pp. 174
-
-
Alberico, D.1
Scott, M.E.2
Lautens, M.3
-
3
-
-
0037094021
-
-
For mechanistic studies on Pd-catalyzed arylation of electron-rich heterocycles, see: a
-
For mechanistic studies on Pd-catalyzed arylation of electron-rich heterocycles, see: (a) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 5286
-
-
Okazawa, T.1
Satoh, T.2
Miura, M.3
Nomura, M.4
-
4
-
-
2342527678
-
-
(b) Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
-
(2004)
Org. Lett
, vol.6
, pp. 1159
-
-
Park, C.-H.1
Ryabova, V.2
Seregin, I.V.3
Sromek, A.W.4
Gevorgyan, V.5
-
5
-
-
20444370318
-
-
(c) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc 2005, 127, 8050.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 8050
-
-
Lane, B.S.1
Brown, M.A.2
Sames, D.3
-
7
-
-
0000882066
-
-
For selected references on Pd-catalyzed arylation and vinylation of electron-rich heterocycles, see: a
-
For selected references on Pd-catalyzed arylation and vinylation of electron-rich heterocycles, see: (a) Ohta, A.; Akita, Y.; Ohkuwa, T.; Chiba, M.; Fukunaga, R.; Miyafuji, A.; Nakata, T.; Tani, N.; Aoyagi, Y. Heterocycles 1990, 31, 1951.
-
(1990)
Heterocycles
, vol.31
, pp. 1951
-
-
Ohta, A.1
Akita, Y.2
Ohkuwa, T.3
Chiba, M.4
Fukunaga, R.5
Miyafuji, A.6
Nakata, T.7
Tani, N.8
Aoyagi, Y.9
-
9
-
-
0001962439
-
-
(c) Lavenot, L.; Gozzi, C.; Ilg, K.; Orlova, I.; Penalva, V.; Lemaire, M. J. Organomet. Chem. 1998, 567, 49.
-
(1998)
J. Organomet. Chem
, vol.567
, pp. 49
-
-
Lavenot, L.1
Gozzi, C.2
Ilg, K.3
Orlova, I.4
Penalva, V.5
Lemaire, M.6
-
10
-
-
0010597557
-
-
(d) Kondo, Y.; Komine, T.; Sakamoto, T. Org. Lett. 2000, 2, 3111.
-
(2000)
Org. Lett
, vol.2
, pp. 3111
-
-
Kondo, Y.1
Komine, T.2
Sakamoto, T.3
-
11
-
-
0037562071
-
-
(e) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. Org. Lett. 2003, 5, 301.
-
(2003)
Org. Lett
, vol.5
, pp. 301
-
-
Glover, B.1
Harvey, K.A.2
Liu, B.3
Sharp, M.J.4
Tymoschenko, M.5
-
12
-
-
0037442583
-
-
(f) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 1700
-
-
Mori, A.1
Sekiguchi, A.2
Masui, K.3
Shimada, T.4
Horie, M.5
Osakada, K.6
Kawamoto, M.7
Ikeda, T.8
-
13
-
-
0345791430
-
-
(g) Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Javadi, G. J.; Cai, D.; Larsen, R. D. Org. Lett. 2003, 5, 4835.
-
(2003)
Org. Lett
, vol.5
, pp. 4835
-
-
Li, W.1
Nelson, D.P.2
Jensen, M.S.3
Hoerrner, R.S.4
Javadi, G.J.5
Cai, D.6
Larsen, R.D.7
-
14
-
-
19844362945
-
-
(h) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino G.; Zoni, C. Eur. J. Org. Chem. 2005, 2091.
-
(2005)
Eur. J. Org. Chem
, pp. 2091
-
-
Beccalli, E.M.1
Broggini, G.2
Martinelli, M.3
Paladino, G.4
Zoni, C.5
-
15
-
-
25444484716
-
-
(i) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 13148
-
-
Bressy, C.1
Alberico, D.2
Lautens, M.3
-
16
-
-
31944442069
-
-
For Pd-catalyzed arylation of electron-defficient heterocycles and simple arenes, see: a
-
For Pd-catalyzed arylation of electron-defficient heterocycles and simple arenes, see: (a) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 1066
-
-
Garcia-Cuadrado, D.1
Braga, A.A.C.2
Maseras, F.3
Echavarren, A.M.4
-
17
-
-
33745959757
-
-
(b) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 8754
-
-
Lafrance, M.1
Rowley, C.N.2
Woo, T.K.3
Fagnou, K.4
-
18
-
-
29844433863
-
-
(c) Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 18020
-
-
Campeau, L.-C.1
Rousseaux, S.2
Fagnou, K.3
-
19
-
-
33845320517
-
-
(d) Leclerc, J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 7781
-
-
Leclerc, J.-P.1
Fagnou, K.2
-
20
-
-
17044366225
-
-
For involvement of Pd(II/IV) catalytic cycle in direct C-H functionalizations, see for example: (a) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
-
For involvement of Pd(II/IV) catalytic cycle in direct C-H functionalizations, see for example: (a) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
-
-
-
-
22
-
-
33646137411
-
-
(c) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 4972
-
-
Deprez, N.R.1
Kalyani, D.2
Krause, A.3
Sanford, M.S.4
-
23
-
-
33745656245
-
-
(a) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 1589
-
-
Lewis, J.C.1
Wu, J.Y.2
Bergman, R.G.3
Ellman, J.A.4
-
24
-
-
17144431294
-
-
(b) Wang, X.; Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 4996
-
-
Wang, X.1
Lane, B.S.2
Sames, D.3
-
25
-
-
33748515918
-
-
(c) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 11748
-
-
Yanagisawa, S.1
Sudo, T.2
Noyori, R.3
Itami, K.4
-
26
-
-
1642281558
-
-
(a) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 3700
-
-
Liu, C.1
Han, X.2
Wang, X.3
Widenhoefer, R.A.4
-
27
-
-
85026866577
-
-
(b) Furstner, A.; Mamane, V.; Seidel, G.; Laurich, D. Org. Synth. 2006, 83, 103.
-
(2006)
Org. Synth
, vol.83
, pp. 103
-
-
Furstner, A.1
Mamane, V.2
Seidel, G.3
Laurich, D.4
-
28
-
-
0034600902
-
-
(a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285.
-
(2000)
Angew. Chem., Int. Ed
, vol.39
, pp. 2285
-
-
Hashmi, A.S.K.1
Schwarz, L.2
Choi, J.-H.3
Frost, T.M.4
-
29
-
-
27644432652
-
-
(b) Li, Z.; Shi, Z.; He, C. J. Organomet. Chem. 2005, 690, 5049.
-
(2005)
J. Organomet. Chem
, vol.690
, pp. 5049
-
-
Li, Z.1
Shi, Z.2
He, C.3
-
30
-
-
0034701226
-
-
(c) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 2661
-
-
Nakamura, I.1
Saito, S.2
Yamamoto, Y.3
-
34
-
-
0037420370
-
-
For the Cu-catalyzed alkynylation of N-H bonds, see: a
-
For the Cu-catalyzed alkynylation of N-H bonds, see: (a) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 2368
-
-
Frederick, M.O.1
Mulder, J.A.2
Tracey, M.R.3
Hsung, R.P.4
Huang, J.5
Kurtz, K.C.M.6
Shen, L.7
Douglas, C.J.8
-
36
-
-
0005891632
-
-
N-fused pyrroloheterocycles are known to be among the most electron-rich heterocyclic cores. See, for example:, Thieme: Stuttgart, Germany, /1, 2a, pp
-
N-fused pyrroloheterocycles are known to be among the most electron-rich heterocyclic cores. See, for example: Behnisch, A.; Behnisch, P.; Eggenweiler, M.; Wallenhorst, T. Indolizine. In Houben-Weyl; Thieme: Stuttgart, Germany, 1994; Vol. E6b/1, 2a, pp 323-450.
-
(1994)
Houben-Weyl
, vol.E6b
, pp. 323-450
-
-
Behnisch, A.1
Behnisch, P.2
Eggenweiler, M.3
-
37
-
-
34347264191
-
-
Trial attempts with non-fused heterocycles, such as pyrroles, under these reaction conditions, afforded low yields of the corresponding alkynylation products. Further studies on the scope of this transformation are underway in our group
-
Trial attempts with non-fused heterocycles, such as pyrroles, under these reaction conditions, afforded low yields of the corresponding alkynylation products. Further studies on the scope of this transformation are underway in our group.
-
-
-
-
38
-
-
34347239747
-
-
For preparation of bromoalkynes, see Supporting Information
-
For preparation of bromoalkynes, see Supporting Information.
-
-
-
-
39
-
-
34347261790
-
-
See Supporting Information for details
-
See Supporting Information for details.
-
-
-
-
40
-
-
0037323519
-
-
Carbon-carbon bond forming reactions proceeding via C-H activation motif usually exhibit much higher KIE. See, for example: Jones, W. D. Acc. Chem. Res. 2003, 36, 140
-
Carbon-carbon bond forming reactions proceeding via C-H activation motif usually exhibit much higher KIE. See, for example: Jones, W. D. Acc. Chem. Res. 2003, 36, 140.
-
-
-
-
41
-
-
34347233520
-
-
The reaction was stopped at 60% conversion to avoid thermal decomposition of the product
-
The reaction was stopped at 60% conversion to avoid thermal decomposition of the product.
-
-
-
|