-
1
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33845375686
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For the discovery of Ni/Cr-mediated coupling reactions, see: (a)
-
For the discovery of Ni/Cr-mediated coupling reactions, see: (a) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644;
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(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 5644
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-
Jin, H.1
Uenishi, J.2
Christ, W.J.3
Kishi, Y.4
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2
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0000959935
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(b) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.
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(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 6048
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-
Takai, K.1
Tagashira, M.2
Kuroda, T.3
Oshima, K.4
Utimoto, K.5
Nozaki, H.6
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3
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28844477490
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-
For cataytic non-asymmetric Cr-mediated coupling reactions, see: (a)
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For cataytic non-asymmetric Cr-mediated coupling reactions, see: (a) Namba, K.; Wang, J.; Cui, S.; Kishi, Y. Org. Lett. 2005, 7, 5421;
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(2005)
Org. Lett.
, vol.7
, pp. 5421
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Namba, K.1
Wang, J.2
Cui, S.3
Kishi, Y.4
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4
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70350329282
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For catalytic asymmetric Cr-mediated coupling reactions, see: (b) and references cited therein
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For catalytic asymmetric Cr-mediated coupling reactions, see: (b) Guo, H.; Dong, C.-G.; Kim, D.-S.; Urabe, D.; Wang, J.; Kim, J. T.; Liu, X.; Sasaki, T.; Kishi, Y. J. Am. Chem. Soc. 2009, 131, 15387. and references cited therein.
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(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 15387
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-
Guo, H.1
Dong, C.-G.2
Kim, D.-S.3
Urabe, D.4
Wang, J.5
Kim, J.T.6
Liu, X.7
Sasaki, T.8
Kishi, Y.9
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5
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0041025238
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(a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908;
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(1971)
J. Am. Chem. Soc.
, vol.93
, pp. 5908
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Semmelhack, M.F.1
Helquist, P.M.2
Jones, L.D.3
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6
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0000016103
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(b) Semmelhack, M. F.; Helquist, P. M.; Gorzynski, J. D. J. Am. Chem. Soc. 1972, 94, 9234.
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(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 9234
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Semmelhack, M.F.1
Helquist, P.M.2
Gorzynski, J.D.3
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7
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0000756083
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Zembayashi, M.; Tamao, K.; Yoshida, J.; Kumada, M. Tetrahedron Lett. 1977, 47, 4089.
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(1977)
Tetrahedron Lett.
, vol.47
, pp. 4089
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Zembayashi, M.1
Tamao, K.2
Yoshida, J.3
Kumada, M.4
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8
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0025328473
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Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80.
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(1990)
Bull. Chem. Soc. Jpn.
, vol.63
, pp. 80
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Iyoda, M.1
Otsuka, H.2
Sato, K.3
Nisato, N.4
Oda, M.5
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9
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79953172299
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For preparation of Ni-catalysts, see Ref. 2
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For preparation of Ni-catalysts, see Ref. 2.
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10
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79953205279
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For abbreviation of ligands, see Figure 2
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For abbreviation of ligands, see Figure 2.
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11
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79953183707
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note
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2 reaches the saturation at 4 mol %.
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12
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79953171226
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note
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3).
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-
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13
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79953173655
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note
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2, the homocoupling of 2-bromopyridine gave approximately 50% conversion for 2 days at room temperature.
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14
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85065137145
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In addition to the classical Ullmann procedure, dipyridyls are prepared via homocoupling of the corresponding halopyridines in the presence of copper, palladium, or nickel complexes. For selected examples, see: Cu-catalyst: (a)
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In addition to the classical Ullmann procedure, dipyridyls are prepared via homocoupling of the corresponding halopyridines in the presence of copper, palladium, or nickel complexes. For selected examples, see: Cu-catalyst: (a) Fanta, P. E. Synthesis 1974, 9;
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(1974)
Synthesis
, pp. 9
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Fanta, P.E.1
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15
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67650578125
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Pd-catalyst: (b)
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Pd-catalyst: (b) Qi, C.; Sun, X.; Lu, C.; Yang, J.; Du, Y.; Wu, H.; Zhang, X.-M. J. Organomet. Chem. 2009, 694, 2912;
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(2009)
J. Organomet. Chem.
, vol.694
, pp. 2912
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Qi, C.1
Sun, X.2
Lu, C.3
Yang, J.4
Du, Y.5
Wu, H.6
Zhang, X.-M.7
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17
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79953211955
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The coupling was not significantly improved by the use of 3-iodopyridine at room temperature
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The coupling was not significantly improved by the use of 3-iodopyridine at room temperature.
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18
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79953202928
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note
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2a However, we were limited in testing a wide range of dipyridyls, because of difficult access to certain dipyridyls.
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19
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79953174016
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note
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2, (E)-1-iodohex-1-ene, (E)-2-iodohex-2-ene, (Z)-1-iodohex-1-ene, and (Z)-2-iodohex-2-ene gave the diene composing of 2.3:1 (E,E):(E,Z), 1.5:1 (E,E):(E,Z), 1:1 (E,E):(E,Z), and 1:5 (E,E):(E,Z), respectively.
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20
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0001424974
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For example, see: (a)
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For example, see: (a) Huggins, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3002;
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(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 3002
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Huggins, J.M.1
Bergman, R.G.2
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21
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65749100789
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(b) Hirata, Y.; Tanaka, M.; Yada, A.; Nakao, Y.; Hiyama, T. Tetrahedron 2009, 65, 5037.
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(2009)
Tetrahedron
, vol.65
, pp. 5037
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Hirata, Y.1
Tanaka, M.2
Yada, A.3
Nakao, Y.4
Hiyama, T.5
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23
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33845374546
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Colon and Amatore proposed the mechanisms also involving Ni(I) and Ni(II) species as the intermediates
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Colon and Amatore proposed the mechanisms also involving Ni(I) and Ni(II) species as the intermediates (Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627;
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(1986)
J. Org. Chem.
, vol.51
, pp. 2627
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Colon, I.1
Kelsey, D.R.2
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25
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79953191532
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note
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2 is a powerful activator for the Pd- or Ni-catalyzed cross-coupling reactions; for example, see Ref. 18.
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-
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28
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33947094318
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and references cited therein
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(c) Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254. and references cited therein.;
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(1978)
J. Am. Chem. Soc.
, vol.100
, pp. 2254
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Negishi, E.1
Okukado, N.2
King, A.O.3
Van Horn, D.E.4
Spiegel, B.I.5
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29
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0000175578
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For the related work from Negishi, see
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For the related work from Negishi, see: Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771;
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(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 10771
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Kondakov, D.Y.1
Negishi, E.2
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31
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41449113700
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Daini, M.; Yamamoto, A.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 2918.
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(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 2918
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Daini, M.1
Yamamoto, A.2
Suginome, M.3
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33
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79953228122
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2, might be involved in the transmetallation
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2, might be involved in the transmetallation.
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34
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0037069728
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Choi, H.; Nakajima, K.; Demeke, D.; Kang, F.-A.; Jun, H.-S.; Wan, Z.-K.; Kishi, Y. Org. Lett. 2002, 4, 4435.
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(2002)
Org. Lett.
, vol.4
, pp. 4435
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Choi, H.1
Nakajima, K.2
Demeke, D.3
Kang, F.-A.4
Jun, H.-S.5
Wan, Z.-K.6
Kishi, Y.7
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