-
4
-
-
33847301925
-
-
For examples of applications by others of Ni/pybox catalysts to cross-coupling reactions of alkyl electrophiles, see: (a) Gong, H, Sinisi, R, Gagne, M. R. J. Am. Chem. Soc. 2007, 129, 1908-1909
-
For examples of applications by others of Ni/pybox catalysts to cross-coupling reactions of alkyl electrophiles, see: (a) Gong, H.; Sinisi, R.; Gagne, M. R. J. Am. Chem. Soc. 2007, 129, 1908-1909.
-
-
-
-
5
-
-
36749022699
-
-
(b) Phapale, V. B.; Bunuel, E.; Garcia-Iglesias, M.; Cardenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790-8795.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 8790-8795
-
-
Phapale, V.B.1
Bunuel, E.2
Garcia-Iglesias, M.3
Cardenas, D.J.4
-
6
-
-
41449104100
-
-
Dai, X.; Strotman, N. A.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302-3303.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 3302-3303
-
-
Dai, X.1
Strotman, N.A.2
Fu, G.C.3
-
8
-
-
13444263825
-
-
For reviews of cross-coupling reactions of alkyl electrophiles, see: a
-
For reviews of cross-coupling reactions of alkyl electrophiles, see: (a) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 674-688
-
-
Frisch, A.C.1
Beller, M.2
-
9
-
-
27844611828
-
-
Tsuji, J, Ed, Springer: New York
-
(b) Netherton, M. R.; Fu, G. C. Topics in Organometallic Chemistry: Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: New York, 2005; pp 85-108.
-
(2005)
Topics in Organometallic Chemistry: Palladium in Organic Synthesis
, pp. 85-108
-
-
Netherton, M.R.1
Fu, G.C.2
-
11
-
-
52449083809
-
-
For two of the pioneering investigations of palladium- and nickel-catalyzed cross-couplings of unactivated alkyl electrophiles, see: (a) Ishiyama, T, Abe, S, Miyaura, N, Suzuki, A. Chem. Lett. 1992, 691-694
-
For two of the pioneering investigations of palladium- and nickel-catalyzed cross-couplings of unactivated alkyl electrophiles, see: (a) Ishiyama, T.; Abe, S.; Miyaura, N.; Suzuki, A. Chem. Lett. 1992, 691-694.
-
-
-
-
12
-
-
33745389166
-
-
(b) Devasagayaraj, A.; Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1995, 34, 2723-2725.
-
(1995)
Angew. Chem., Int. Ed. Engl
, vol.34
, pp. 2723-2725
-
-
Devasagayaraj, A.1
Stüdemann, T.2
Knochel, P.3
-
13
-
-
33749519198
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-
For mechanistic studies of nickel-catalyzed couplings of unactivated alkyl electrophiles, see: a
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For mechanistic studies of nickel-catalyzed couplings of unactivated alkyl electrophiles, see: (a) Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175-13183.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 13175-13183
-
-
Jones, G.D.1
Martin, J.L.2
McFarland, C.3
Allen, O.R.4
Hall, R.E.5
Haley, A.D.6
Brandon, R.J.7
Konovalova, T.8
Desrochers, P.J.9
Pulay, P.10
Vicic, D.A.11
-
15
-
-
84891029339
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-
For some leading references to the chemistry of alkynes, see: a, Diederich, F, Stang, P. J, Tykwinski, R. R, Eds, Wiley-VCH: New York
-
For some leading references to the chemistry of alkynes, see: (a) Acetylene Chemistry; Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: New York, 2005.
-
(2005)
Acetylene Chemistry
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-
-
17
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80055045239
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-
For a review of the Negishi reaction, see: a, Rappoport, Z, Marek, I, Eds, Wiley: New York, Chapter 11
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For a review of the Negishi reaction, see: (a) Negishi, E.-i.; Hu, Q.; Huang, Z.; Wang, G.; Yin, N. In The Chemistry of Organozinc Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: New York, 2006; Chapter 11.
-
(2006)
The Chemistry of Organozinc Compounds
-
-
Negishi, E.-I.1
Hu, Q.2
Huang, Z.3
Wang, G.4
Yin, N.5
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18
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52449123290
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For nickel-catalyzed asymmetric cross-coupling reactions of alkyl electrophiles, we have generally found that the use of a slight excess of ligand, relative to nickel, leads to improved yield and/or ee
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For nickel-catalyzed asymmetric cross-coupling reactions of alkyl electrophiles, we have generally found that the use of a slight excess of ligand, relative to nickel, leads to improved yield and/or ee.
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19
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52449118387
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Better, but still unsatisfactory, results were obtained if the magnesium/lithium salts were removed prior to cross-coupling
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Better, but still unsatisfactory, results were obtained if the magnesium/lithium salts were removed prior to cross-coupling.
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21
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33745760081
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(b) Schmidt, F.; Stemmler, R. T.; Rudolph, J.; Bolm, C. Chem. Soc. Rev. 2006, 35, 454-470.
-
(2006)
Chem. Soc. Rev
, vol.35
, pp. 454-470
-
-
Schmidt, F.1
Stemmler, R.T.2
Rudolph, J.3
Bolm, C.4
-
22
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38849092076
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For a discussion of boron-to-zinc transmetalation, see: ca
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(c) For a discussion of boron-to-zinc transmetalation, see: (ca) Jimeno, C.; Sayalero, S.; Fjermestad, T.; Colet, G.; Maseras, F.; Pericas, M. A. Angew. Chem., Int. Ed. 2008, 47, 1098-1101.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 1098-1101
-
-
Jimeno, C.1
Sayalero, S.2
Fjermestad, T.3
Colet, G.4
Maseras, F.5
Pericas, M.A.6
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23
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52449099717
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2·glyme or pybox ligand 1, essentially none of the desired alkyne is formed.
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2·glyme or pybox ligand 1, essentially none of the desired alkyne is formed.
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24
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52449119513
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Palladium-catalyzed cross-couplings of propargylic electrophiles with organometallic reagents typically furnish the allene, not the alkyne, as the major product. See: (a) Tsuji, J, Mandai, T. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A, Diederich, F, Eds, Wiley-VCH: New York, 2004; Chapter 10;
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Palladium-catalyzed cross-couplings of propargylic electrophiles with organometallic reagents typically furnish the allene, not the alkyne, as the major product. See: (a) Tsuji, J.; Mandai, T. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York, 2004; Chapter 10;
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25
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4544245050
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Ma, S. Eur. J. Org. Chem. 2004, 1175-1183. The regioselectivity of carbon-carbon bond formation for the corresponding nickel-catalyzed processes has not been thoroughly investigated. For all of the Negishi reaction catalyzed by Ni/1 that are reported herein, essentially none of the allene is formed (<5%), regardless of the choice of R.
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Ma, S. Eur. J. Org. Chem. 2004, 1175-1183. The regioselectivity of carbon-carbon bond formation for the corresponding nickel-catalyzed processes has not been thoroughly investigated. For all of the Negishi reaction catalyzed by Ni/1 that are reported herein, essentially none of the allene is formed (<5%), regardless of the choice of R.
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Pelphrey, P. M.; Popov, V. M.; Joska, T. M.; Beierlein, J. M.; Bolstad, E. S. D.; Fillingham, Y. A.; Wright, D. L.; Anderson, A. C. J. Med. Chem. 2007, 50, 940-950.
-
(2007)
J. Med. Chem
, vol.50
, pp. 940-950
-
-
Pelphrey, P.M.1
Popov, V.M.2
Joska, T.M.3
Beierlein, J.M.4
Bolstad, E.S.D.5
Fillingham, Y.A.6
Wright, D.L.7
Anderson, A.C.8
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