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1
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0003397781
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Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York
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For reviews on this topic, see: (a) Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
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Metal-catalyzed Cross-coupling Reactions
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2
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0036589259
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(b) Hassa, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
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Chem. Rev.
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Hassa, J.1
Sevignon, M.2
Gozzi, C.3
Schulz, E.4
Lemaire, M.5
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4
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2342527678
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(b) Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
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Org. Lett.
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Park, C.-H.1
Ryabova, V.2
Seregin, I.V.3
Sromek, A.W.4
Gevorgyan, V.5
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5
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0037562071
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(c) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. Org. Lett. 2003, 5, 301.
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Org. Lett.
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Glover, B.1
Harvey, K.A.2
Liu, B.3
Sharp, M.J.4
Tymoschenko, M.5
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6
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0037094021
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(d) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
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J. Am. Chem. Soc.
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Okazawa, T.1
Satoh, T.2
Miura, M.3
Nomura, M.4
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7
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0347296197
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Current reactions require the presence of an activating or directing group. For example, see: (a) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
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Angew. Chem., Int. Ed.
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Bedford, R.B.1
Coles, S.J.2
Hursthouse, M.B.3
Limmert, M.E.4
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8
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0030776292
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(b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
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Angew. Chem., Int. Ed. Engl.
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Satoh, T.1
Kawamura, Y.2
Miura, M.3
Nomura, M.4
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9
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0037442914
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(c) Kakiuchi, F.; Kan, S.; Igi, K. Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
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J. Am. Chem. Soc.
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Kakiuchi, F.1
Kan, S.2
Igi, K.3
Chatani, N.4
Murai, S.5
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10
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0034620911
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(d) Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655.
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Tetrahedron Lett.
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Kametani, Y.1
Satoh, T.2
Miura, M.3
Nomura, M.4
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12
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0242352421
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and references therein
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(f) Oi, S.; Watanabe, S.-i.; Fukita, S.; Inoue, Y. Tetrahedron Lett. 2003, 44, 8665 and references therein.
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Tetrahedron Lett.
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, pp. 8665
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Oi, S.1
Watanabe, S.-I.2
Fukita, S.3
Inoue, Y.4
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13
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0033519228
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With 30 mol % catalyst: (a) Kitamura, M.; Ohmori, K.; Kawase, T.; Suzuki, K. Angew. Chem., Int. Ed. 1999, 38, 1229.
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(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 1229
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Kitamura, M.1
Ohmori, K.2
Kawase, T.3
Suzuki, K.4
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14
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0000580013
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(b) Rice, J. E.; Cai, Z.-W.; He, Z.-M.; LaVaoie, E. J. J. Org. Chem. 1995, 60, 8101. With 26 mol % catalyst:
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(1995)
J. Org. Chem.
, vol.60
, pp. 8101
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Rice, J.E.1
Cai, Z.-W.2
He, Z.-M.3
LaVaoie, E.J.4
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15
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0028209470
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(c) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. With 25 mol % catalyst:
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(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 1004
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Hosoya, T.1
Takashiro, E.2
Matsumoto, T.3
Suzuki, K.4
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16
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0026590352
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(d) Matsumoto, T.; Hosoya, T.; Suzuki, K. J. Am. Chem. Soc. 1992, 114, 3568. With 20-25 mol % catalyst:
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(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 3568
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Matsumoto, T.1
Hosoya, T.2
Suzuki, K.3
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19
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0033975522
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(g) Bringmann, G.; Heubes, M.; Breuning, M.; Gobel, L.; Ochse, M.; Schoner, B.; Schupp, O. J. Org. Chem. 2000, 65, 722.
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J. Org. Chem.
, vol.65
, pp. 722
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Bringmann, G.1
Heubes, M.2
Breuning, M.3
Gobel, L.4
Ochse, M.5
Schoner, B.6
Schupp, O.7
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20
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0034616313
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(h) Bringmann, G.; Ochse, M.; Gotz, R. J. Org. Chem. 2000, 65, 2069.
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J. Org. Chem.
, vol.65
, pp. 2069
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Bringmann, G.1
Ochse, M.2
Gotz, R.3
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21
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0002045168
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(i) Harayama, T.; Yasuda, H. Heterocycles 1997, 46, 61. Larock has reported a catalyst system that has been used with 5 mol % loading in analogous processes:
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(1997)
Heterocycles
, vol.46
, pp. 61
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Harayama, T.1
Yasuda, H.2
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22
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0141645589
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(j) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506.
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J. Am. Chem. Soc.
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, pp. 11506
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Campo, M.A.1
Huang, Q.2
Yao, T.3
Tian, Q.4
Larock, R.C.5
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23
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0034639684
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Futagami, S.; Ohashi, Y.; Imura, K.; Hosoya, T.; Ohmori, K.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 2000, 41, 1063.
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Tetrahedron Lett.
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, pp. 1063
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-
Futagami, S.1
Ohashi, Y.2
Imura, K.3
Hosoya, T.4
Ohmori, K.5
Matsumoto, T.6
Suzuki, K.7
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24
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2942643950
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After the submission of this manuscript, Larock reported tandem reactions producing five-membered rings using 5 mol % catalyst. See: Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
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J. Am. Chem. Soc.
, vol.126
, pp. 7460
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-
Huang, Q.1
Fazio, A.2
Dai, G.3
Campo, M.A.4
Larock, R.C.5
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25
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0031013608
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See also refs 3a, 3b, and 4e
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(a) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. See also refs 3a, 3b, and 4e.
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J. Org. Chem.
, vol.62
, pp. 2
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Hennings, D.D.1
Iwasa, S.2
Rawal, V.H.3
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27
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3342930871
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note
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3 (2 equiv) at 95 °C in a Labmate heater shaker.
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28
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0033529898
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Harris, M. C.; Geis, O.; Buchwald, S. L. J. Org. Chem. 1999, 64, 6019. This ligand is commericially available from Strem Chemicals.
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(1999)
J. Org. Chem.
, vol.64
, pp. 6019
-
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Harris, M.C.1
Geis, O.2
Buchwald, S.L.3
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29
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3342930870
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note
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This decreased reactivity in the absence of a heteroatom has previously been observed. See reference 4j.
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-
-
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30
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3242659154
-
-
and references therein
-
For a recent highlight on this topic, see: Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201 and references therein.
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(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 2201
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Miura, M.1
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31
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3342944704
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note
-
Both oxidative insertion into the aryl C-H bond to give a hydridopallada-(IV)cycle and electrophilic addition/deprotonation to give a pallada(II)-cycle have previously been proposed for analogous processes. For example, see ref 6 and references therein.
-
-
-
-
32
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3342934488
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note
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See the Supporting Information.
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33
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0035354658
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(a) Martin-Matute, B.; Mateo, C.; Cardenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2001, 7, 2341.
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Chem. Eur. J.
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Martin-Matute, B.1
Mateo, C.2
Cardenas, D.J.3
Echavarren, A.M.4
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