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(c) Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
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(b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
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(c) Baxendale, I. R.; Griffiths-Jones, C. M.; Ley, S. V.; Tranmer, G. C. Chem. - Eur. J. 2006, 12, 4407.
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Baxendale, I.R.1
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14
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1842452582
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For selected examples highlighting the problems with the use of organoboron reagents, see: a
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For selected examples highlighting the problems with the use of organoboron reagents, see: (a) Handy, S. T.; Zhang, Y.; Bregman, H. J. Org. Chem. 2004, 69, 2362.
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J. Org. Chem
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Handy, S.T.1
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0034554740
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(b) Chaumeil, H.; Signorella, S.; Le Drian, C. Tetrahedron 2000, 56, 9655.
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Tetrahedron
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Chaumeil, H.1
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Le Drian, C.3
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17
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33847086004
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(a) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
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(1980)
J. Am. Chem. Soc
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Negishi, E.1
Valente, L.F.2
Kobayashi, M.3
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19
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4043088534
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(c) Zeng, X.; Quian, M.; Hu, Q.; Negishi, E. Angew. Chem., Int. Ed. 2004, 43, 2259.
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Angew. Chem., Int. Ed
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Zeng, X.1
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Negishi, E.4
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20
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55249105544
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Manolikakes, G.; Schade, M. A.; Muñoz Hernandez, C.; Mayr, H.; Knochel, P. Org. Lett. 2008, 10, 2765.
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Org. Lett
, vol.10
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Manolikakes, G.1
Schade, M.A.2
Muñoz Hernandez, C.3
Mayr, H.4
Knochel, P.5
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21
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33748805474
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The preparation of the zinc reagent by transmetalation from the corresponding organomagnesium or organolithium compound led to similar results. For the preperation via direct zinc insertion, see: Krasovskiy, A, Malakhov, V, Gavryushin, A, Knochel, P. Angew. Chem, Int. Ed. 2006, 45, 6040
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The preparation of the zinc reagent by transmetalation from the corresponding organomagnesium or organolithium compound led to similar results. For the preperation via direct zinc insertion, see: Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040.
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22
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33745453356
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Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. Chem. - Eur. J. 2006, 12, 4749.
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Chem. - Eur. J
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, pp. 4749
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Organ, M.G.1
Avola, S.2
Dubovyk, I.3
Hadei, N.4
Kantchev, E.A.B.5
O'Brien, C.J.6
Valente, C.7
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26
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16844367937
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S-Phos (L3) was purchased from Strem or prepared according to: Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
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S-Phos (L3) was purchased from Strem or prepared according to: Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
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27
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55249084525
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a data see: http:// www.chem.wisc.edu/areas/reich/pkatable/ index.htm and references cited therein.
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a data see: http:// www.chem.wisc.edu/areas/reich/pkatable/ index.htm and references cited therein.
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28
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46149094730
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Metzger, A.; Schade, M. A.; Knochel, P. Org. Lett. 2008, 10, 1107.
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(2008)
Org. Lett
, vol.10
, pp. 1107
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Metzger, A.1
Schade, M.A.2
Knochel, P.3
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29
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35348925613
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Boros, E. E.; Burova, S. A.; Erickson, G. A; Johns, B. A.; Koble, C. S.; Kurose, N.; Sharp, M. J.; Tabet, E. A.; Thompson, J. B.; Toczko, M. A. Org. Process Res. Dev. 2007, 11, 899.
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Boros, E. E.; Burova, S. A.; Erickson, G. A; Johns, B. A.; Koble, C. S.; Kurose, N.; Sharp, M. J.; Tabet, E. A.; Thompson, J. B.; Toczko, M. A. Org. Process Res. Dev. 2007, 11, 899.
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30
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4544311534
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However, for the coupling of 5-bromoindole (7), the zinc reagents 1a, 1g, and 1h had to be prepared by transmetalation from the corresponding magnesium reagents. Control experiments have revealed accelerated cross-coupling reactions in the presence of magnesium salts. For the preparation of organomagnesium reagents, see: (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
-
However, for the coupling of 5-bromoindole (7), the zinc reagents 1a, 1g, and 1h had to be prepared by transmetalation from the corresponding magnesium reagents. Control experiments have revealed accelerated cross-coupling reactions in the presence of magnesium salts. For the preparation of organomagnesium reagents, see: (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
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31
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0141645562
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(b) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302.
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(2003)
Angew. Chem., Int. Ed
, vol.42
, pp. 4302
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Knochel, P.1
Dohle, W.2
Gommermann, N.3
Kneisel, F.4
Kopp, F.5
Korn, T.6
Sapountzis, I.7
Vu, V.A.8
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32
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0003445429
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Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin
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Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
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(1999)
Comprehensive Asymmetric Catalysis
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33
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38349143429
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(a) Melzig, L.; Gavryushin, A.; Knochel, P. Org. Lett. 2007, 9, 5529.
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(2007)
Org. Lett
, vol.9
, pp. 5529
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Melzig, L.1
Gavryushin, A.2
Knochel, P.3
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34
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0032927129
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(b) Giovannini, R.; Stüdemann, T.; Dussin, G.; Knochel, P. J. Org. Chem. 1999, 64, 3544.
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(1999)
J. Org. Chem
, vol.64
, pp. 3544
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Giovannini, R.1
Stüdemann, T.2
Dussin, G.3
Knochel, P.4
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35
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0345404157
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(c) Giovannini, R.; Stüdemann, T.; Dussin, G.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 2387.
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(1998)
Angew. Chem., Int. Ed
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, pp. 2387
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Giovannini, R.1
Stüdemann, T.2
Dussin, G.3
Knochel, P.4
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36
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27644540188
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Gavryushin, A.; Kofink, C.; Manolikakes, G.; Knochel, P. Org. Lett. 2005, 7, 4871.
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(2005)
Org. Lett
, vol.7
, pp. 4871
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Gavryushin, A.1
Kofink, C.2
Manolikakes, G.3
Knochel, P.4
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37
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55249122769
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3 (0.07 euro/g) were purchased from Alfa Aesar, L3 (139.50 euro/g) from Strem.
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3 (0.07 euro/g) were purchased from Alfa Aesar, L3 (139.50 euro/g) from Strem.
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38
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0038732070
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For the reactivity of 1,1-bimetallic species towards protonation, see also: Knochel, P.; Normant, J. F. Tetrahedron Lett. 1986, 27, 1043.
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For the reactivity of 1,1-bimetallic species towards protonation, see also: Knochel, P.; Normant, J. F. Tetrahedron Lett. 1986, 27, 1043.
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39
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0001049972
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For the preparation of zinc and copper organometallics bearing acidic hydrogens, see
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For the preparation of zinc and copper organometallics bearing acidic hydrogens, see: Knoess, H. P.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1991, 56, 5974.
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(1991)
J. Org. Chem
, vol.56
, pp. 5974
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Knoess, H.P.1
Rozema, M.J.2
Knochel, P.3
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40
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55249085695
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Using OctZnI·LiCl or PhCH2ZnCl·LiCl led to similar results
-
2ZnCl·LiCl led to similar results.
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41
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0004219714
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2nd ed, Schlosser, M, Ed, Wiley: Chichester, UK
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Organometallics in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, UK, 2002.
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(2002)
Organometallics in Synthesis: A Manual
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