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1
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0003397781
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-
For early reviews, see: a, Diederich, F, Stang, P. J. Eds, Wiley-VCH: New York
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For early reviews, see: (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J. Eds.; Wiley-VCH: New York, 1998.
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(1998)
Metal-Catalyzed Cross-Coupling Reactions
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4
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20544450502
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de Meijere, A, Diederich, F. Eds, Wiley-VCH: New York
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(b) Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F. Eds.; Wiley-VCH: New York, 2004.
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(2004)
Metal-Catalyzed Cross-Coupling Reactions
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7
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0037112673
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Palladium-Catalyzed Coupling Reactions of Aryl Chlorides
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For reviews of coupling reactions of aryl chlorides, see: a
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For reviews of coupling reactions of aryl chlorides, see: (a) Littke, A. F.; Fu, G. C. Palladium-Catalyzed Coupling Reactions of Aryl Chlorides. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
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(2002)
Angew. Chem., Int. Ed
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Littke, A.F.1
Fu, G.C.2
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8
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0003028264
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Activation of Otherwise Unreactive C-Cl Bonds
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Murai, S. Ed, Springer-Verlag: Berlin
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(b) Grushin, V. V.; Alper, H. Activation of Otherwise Unreactive C-Cl Bonds. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S. Ed.; Springer-Verlag: Berlin, 1999; pp 193-226.
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(1999)
Activation of Unreactive Bonds and Organic Synthesis
, pp. 193-226
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Grushin, V.V.1
Alper, H.2
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9
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57549088537
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During the past decade, powerful new catalysts for coupling reactions have been developed by a number of groups. Due to space limitations, it will not be possible to summarize in this Account the exciting discoveries of other laboratories. For an overview of early work, see ref 3a
-
During the past decade, powerful new catalysts for coupling reactions have been developed by a number of groups. Due to space limitations, it will not be possible to summarize in this Account the exciting discoveries of other laboratories. For an overview of early work, see ref 3a.
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11
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0029788478
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Diphenylphosphidoboratabenzene: An Anionic Analogue of Triphenylphosphine
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Hoic, D. A.; Davis, W. M.; Fu, G. C. Diphenylphosphidoboratabenzene: An Anionic Analogue of Triphenylphosphine. J. Am. Chem. Soc. 1996, 118, 8176-8177.
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J. Am. Chem. Soc
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Hoic, D.A.1
Davis, W.M.2
Fu, G.C.3
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12
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0034127063
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Anionic Pd(0) and Pd(II) Intermediates in Palladium-Catalyzed Heck and Cross-Coupling Reactions
-
For a discussion of the role of anionic palladium complexes in coupling reactions, see
-
For a discussion of the role of anionic palladium complexes in coupling reactions, see: Amatore, C.; Jutand, A. Anionic Pd(0) and Pd(II) Intermediates in Palladium-Catalyzed Heck and Cross-Coupling Reactions. Acc. Chem. Res. 2000, 33, 314-321.
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Acc. Chem. Res
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Amatore, C.1
Jutand, A.2
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13
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57549084888
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For reviews, see: (a) Miyaura, N. Metal-Catalyzed Cross-Coupling Reactions of Organoboron Compounds with Organic Halides. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F. Eds.; Wiley-VCH: New York, 2004; Chapter 2.
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For reviews, see: (a) Miyaura, N. Metal-Catalyzed Cross-Coupling Reactions of Organoboron Compounds with Organic Halides. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F. Eds.; Wiley-VCH: New York, 2004; Chapter 2.
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14
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57549103010
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Suzuki, A. Overview of the Suzuki Protocol with B. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i. Ed.; Wiley Interscience: New York, 2002; Chapter III.2.2.
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(b) Suzuki, A. Overview of the Suzuki Protocol with B. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i. Ed.; Wiley Interscience: New York, 2002; Chapter III.2.2.
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15
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0033521580
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A Convenient and General Method for Palladium-Catalyzed Suzuki Cross-Couplings of Aryl Chlorides and Arylboronic Acids
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(a) Littke, A. F.; Fu, G. C. A Convenient and General Method for Palladium-Catalyzed Suzuki Cross-Couplings of Aryl Chlorides and Arylboronic Acids. Angew. Chem., Int. Ed. 1998, 37, 3387-3388.
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Angew. Chem., Int. Ed
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Littke, A.F.1
Fu, G.C.2
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16
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0034600318
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Littke, A. F.; Dai, C.; Fu, G. C. Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions. J. Am. Chem. Soc. 2000, 122, 4020-4028.
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(b) Littke, A. F.; Dai, C.; Fu, G. C. Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions. J. Am. Chem. Soc. 2000, 122, 4020-4028.
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17
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0032560932
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My colleague Steve Buchwald has established that bulky dialkylarylphosphines also provide active catalysts, and he was the first to report palladium-catalyzed Suzuki reactions of unactivated aryl chlorides. Old, D. W, Wolfe, J. P, Buchwald, S. L. A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides. J. Am. Chem. Soc. 1998, 120, 9722-9723
-
My colleague Steve Buchwald has established that bulky dialkylarylphosphines also provide active catalysts, and he was the first to report palladium-catalyzed Suzuki reactions of unactivated aryl chlorides. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides. J. Am. Chem. Soc. 1998, 120, 9722-9723.
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18
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0037393778
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3 in a wide range of palladium-catalyzed coupling reactions. For one overview of his many contributions, see: Culkin, D. A.; Hartwig, J. F. Palladium-Catalyzed α-Arylation of Carbonyl Compounds and Nitriles. Acc. Chem. Res. 2003, 36, 234-245.
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3 in a wide range of palladium-catalyzed coupling reactions. For one overview of his many contributions, see: Culkin, D. A.; Hartwig, J. F. Palladium-Catalyzed α-Arylation of Carbonyl Compounds and Nitriles. Acc. Chem. Res. 2003, 36, 234-245.
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19
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0000728442
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Synthesis of Biaryls via a Nickel(0)-Catalyzed Cross-Coupling Reaction of Chloroarenes with Arylboronic Acids
-
For pioneering work on nickel-catalyzed processes, see: a
-
For pioneering work on nickel-catalyzed processes, see: (a) Saito, S.; Oh-tani, S.; Miyaura, N. Synthesis of Biaryls via a Nickel(0)-Catalyzed Cross-Coupling Reaction of Chloroarenes with Arylboronic Acids. J. Org. Chem. 1997, 62, 8024-8030.
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Saito, S.1
Oh-tani, S.2
Miyaura, N.3
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20
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0030921405
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Suzuki-Type Coupling of Chloroarenes with Arylboronic Acids Catalysed by Nickel Complexes
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(b) Indolese, A. F. Suzuki-Type Coupling of Chloroarenes with Arylboronic Acids Catalysed by Nickel Complexes. Tetrahedron Lett. 1997, 38, 3513-3516.
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Indolese, A.F.1
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21
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Shen, W. Palladium Catalyzed Coupling of Aryl Chlorides with Arylboronic Acids. Tetrahedron Lett. 1997, 38, 5575-5578.
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Tetrahedron Lett
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Shen, W.1
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22
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0032510005
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Synthesis of N-Arylpiperazines from Aryl Halides and Piperazine under a Palladium Tri-tert-butylphosphine Catalyst
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Nishiyama, M.; Yamamoto, T.; Koie, Y. Synthesis of N-Arylpiperazines from Aryl Halides and Piperazine under a Palladium Tri-tert-butylphosphine Catalyst. Tetrahedron Lett. 1998, 33, 617-620.
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Tetrahedron Lett
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Nishiyama, M.1
Yamamoto, T.2
Koie, Y.3
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23
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0001104162
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In addition, Milstein had reported the use of a chelating bis(trialkylphosphine) in Heck reactions of aryl chlorides: Ben-David, Y, Portnoy, M, Gozin, M, Milstein, D. Palladium-Catalyzed Vinylation of Aryl Chlorides. Chelate Effect in Catalysis. Organometallics 1992, 11, 1995-1996
-
In addition, Milstein had reported the use of a chelating bis(trialkylphosphine) in Heck reactions of aryl chlorides: Ben-David, Y.; Portnoy, M.; Gozin, M.; Milstein, D. Palladium-Catalyzed Vinylation of Aryl Chlorides. Chelate Effect in Catalysis. Organometallics 1992, 11, 1995-1996.
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24
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33751158485
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Fluoride-Mediated Boronic Acid Coupling Reactions
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Wright, S. W.; Hageman, D. L.; McClure, L. D. Fluoride-Mediated Boronic Acid Coupling Reactions. J. Org. Chem. 1994, 59, 6095-6097.
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Wright, S.W.1
Hageman, D.L.2
McClure, L.D.3
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25
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33745721269
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A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles
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Kudo, N.; Perseghini, M.; Fu, G. C. A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles. Angew. Chem., Int. Ed. 2006, 45, 1282-1284.
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Kudo, N.1
Perseghini, M.2
Fu, G.C.3
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26
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12344337689
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Monoligated Palladium Species as Catalysts in Cross-Coupling Reactions
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Christmann, U.; Vilar, R. Monoligated Palladium Species as Catalysts in Cross-Coupling Reactions. Angew. Chem., Int. Ed. 2005, 44, 366-374.
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, pp. 366-374
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Christmann, U.1
Vilar, R.2
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27
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33846588529
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For a few examples, see: (a) Noguchi, H.; Hojo, K.; Suginome, M. Boron-Masking Strategy for the Selective Synthesis of Oligoarenes via Iterative Suzuki-Miyaura Coupling. J. Am. Chem. Soc. 2007, 129, 758-759.
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For a few examples, see: (a) Noguchi, H.; Hojo, K.; Suginome, M. Boron-Masking Strategy for the Selective Synthesis of Oligoarenes via Iterative Suzuki-Miyaura Coupling. J. Am. Chem. Soc. 2007, 129, 758-759.
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28
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34250840712
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Chain-Growth Polymerization for the Synthesis of Polyfluorene via Suzuki-Miyaura Coupling Reaction from an Externally Added Initiator Unit
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(b) Yokoyama, A.; Suzuki, H.; Kubota, Y.; Ohuchi, K.; Higashimura, H.; Yokozawa, T. Chain-Growth Polymerization for the Synthesis of Polyfluorene via Suzuki-Miyaura Coupling Reaction from an Externally Added Initiator Unit. J. Am. Chem. Soc. 2007, 129, 7236-7237.
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Yokoyama, A.1
Suzuki, H.2
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Ohuchi, K.4
Higashimura, H.5
Yokozawa, T.6
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29
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20444468523
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Practical Application of New Catalytic Methods: A Concise Synthesis of a Potent PDE IV Inhibitor
-
For a kilogram-scale reaction, see
-
(c) For a kilogram-scale reaction, see: Albaneze-Walker, J.; Murry, J. A.; Soheili, A.; Ceglia, S.; Springfield, S. A.; Bazaral, C.; Dormer, P. G.; Hughes, D. L. Practical Application of New Catalytic Methods: A Concise Synthesis of a Potent PDE IV Inhibitor. Tetrahedron 2005, 61, 6330-6336.
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(2005)
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Albaneze-Walker, J.1
Murry, J.A.2
Soheili, A.3
Ceglia, S.4
Springfield, S.A.5
Bazaral, C.6
Dormer, P.G.7
Hughes, D.L.8
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30
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14344266665
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Organotin Reagents in Cross-Coupling Reactions
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For reviews, see: a, de Meijere, A, Diederich, F. Eds, Wiley-VCH: New York, Chapter 3
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For reviews, see: (a) Mitchell, T. N. Organotin Reagents in Cross-Coupling Reactions. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F. Eds.; Wiley-VCH: New York, 2004; Chapter 3.
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Mitchell, T.N.1
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31
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57549108909
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Kosugi, M.; Fugami, K. Overview of the Stille Protocol with Sn. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley Interscience: New York, 2002; Chapter III.2.3.
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(b) Kosugi, M.; Fugami, K. Overview of the Stille Protocol with Sn. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley Interscience: New York, 2002; Chapter III.2.3.
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32
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Reaction: An Important Tool in the Synthesis of Complex Natural Products
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(c) De Souza, M. V. N. Stille Reaction: An Important Tool in the Synthesis of Complex Natural Products. Curr. Org. Synth. 2006, 3, 313-326.
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Souza, D.1
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33
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33748731943
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Nickel-Catalysed Cross-Coupling Reactions of Aryl Halides with Organostannanes
-
For an early report of a nickel-based catalyst, see
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For an early report of a nickel-based catalyst, see: Shirakawa, E.; Yamasaki, K.; Hiyama, T. Nickel-Catalysed Cross-Coupling Reactions of Aryl Halides with Organostannanes. J. Chem. Soc., Perkin Trans. 1 1997, 2449-2450.
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Shirakawa, E.1
Yamasaki, K.2
Hiyama, T.3
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0033549832
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The First General Method for Stille Cross-Couplings of Aryl Chlorides
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(a) Littke, A. F.; Fu, G. C. The First General Method for Stille Cross-Couplings of Aryl Chlorides. Angew. Chem., Int. Ed. 1999, 38, 2411-2413.
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Littke, A.F.1
Fu, G.C.2
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35
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0037024173
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3: A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides
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3: A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides. J. Am. Chem. Soc. 2002, 124, 6343-6348.
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Littke, A.F.1
Schwarz, L.2
Fu, G.C.3
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36
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0041365858
-
Total Synthesis of Anti-HIV Agent Chloropeptin I
-
The overall yield for the cross-coupling and two other steps was 40
-
Deng, H.; Jung, J.-K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Total Synthesis of Anti-HIV Agent Chloropeptin I. J. Am. Chem. Soc. 2003, 125, 9032-9034. The overall yield for the cross-coupling and two other steps was 40%.
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Deng, H.1
Jung, J.-K.2
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Snapper, M.L.5
Hoveyda, A.H.6
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37
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33845924762
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3 in Stille cross-couplings, see: (a) Cook, S. P.; Polara, A.; Danishefsky, S. J. The Total Synthesis of (±)-11-O-Debenzoyltashironin. J. Am. Chem. Soc. 2006, 128, 16440-16441.
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3 in Stille cross-couplings, see: (a) Cook, S. P.; Polara, A.; Danishefsky, S. J. The Total Synthesis of (±)-11-O-Debenzoyltashironin. J. Am. Chem. Soc. 2006, 128, 16440-16441.
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38
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33748512153
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Total Synthesis of Piericidin A1 and B1 and Key Analogues
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(b) Schnermann, M. J.; Romero, F. A.; Hwang, I.; Nakamaru-Ogiso, E.; Yagi, T.; Boger, D. L. Total Synthesis of Piericidin A1 and B1 and Key Analogues. J. Am. Chem. Soc. 2006, 128, 11799-11807.
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Schnermann, M.J.1
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39
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15744392259
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p-Channel Organic Semiconductors Based on Hybrid Acene-Thiophene Molecules for Thin-Film Transistor Applications
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(c) Merlo, J. A.; Newman, C. R.; Gerlach, C. P.; Kelley, T. W.; Muyres, D. V.; Fritz, S. E.; Toney, M. F.; Frisbie, C. D. p-Channel Organic Semiconductors Based on Hybrid Acene-Thiophene Molecules for Thin-Film Transistor Applications. J. Am. Chem. Soc. 2005, 127, 3997-4009.
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Fritz, S.E.6
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40
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Palladium- or Nickel-Catalyzed Cross-Coupling Reactions with Organozincs and Related Organometals
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For a review, see:, Rappoport, Z, Marek, I. Eds, Wiley: New York, Chapter 11
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For a review, see: Negishi, E.-i.; Hu, Q.; Huang, Z.; Wang, G.; Yin, N. Palladium- or Nickel-Catalyzed Cross-Coupling Reactions with Organozincs and Related Organometals. In The Chemistry of Organozinc Compounds; Rappoport, Z., Marek, I. Eds.; Wiley: New York, 2006; Chapter 11.
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0011404901
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Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. Bis(tertiary phosphine)palladium(0) and -platinum(0) Complexes: Preparations and Crystal and Molecular Structures. J. Am. Chem. Soc. 1976, 98, 5850-5858.
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43
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57549088713
-
-
2 is sold by a variety of suppliers, including Strem, Aldrich, and Alfa-Aesar.
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2 is sold by a variety of suppliers, including Strem, Aldrich, and Alfa-Aesar.
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44
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0034812321
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2 as a Catalyst. J. Am. Chem. Soc. 2001, 123, 2719-2724.
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2 as a Catalyst. J. Am. Chem. Soc. 2001, 123, 2719-2724.
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45
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33746216351
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Stereoselective Synthesis of the Side Chains of Mycolactones A and B Featuring Stepwise Double Substitutions of 1,1-Dibromo-1-alkenes
-
For example, see
-
For example, see: Yin, N.; Wang, G.; Qian, M.; Negishi, E. Stereoselective Synthesis of the Side Chains of Mycolactones A and B Featuring Stepwise Double Substitutions of 1,1-Dibromo-1-alkenes. Angew. Chem., Int. Ed. 2006, 45, 2916-2920.
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Yin, N.1
Wang, G.2
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Negishi, E.4
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46
-
-
34848839222
-
-
For eq 8, see: Tsuji, H.; Mitsui, C.; Ilies, L.; Sato, Y.; Nakamura, E. Synthesis and Properties of 2,3,6,7-Tetraarylbenzo[1,2-b:4,5-b′]difurans as Hole-Transporting Material. J. Am. Chem. Soc. 2007, 129, 11902-11903.
-
For eq 8, see: Tsuji, H.; Mitsui, C.; Ilies, L.; Sato, Y.; Nakamura, E. Synthesis and Properties of 2,3,6,7-Tetraarylbenzo[1,2-b:4,5-b′]difurans as Hole-Transporting Material. J. Am. Chem. Soc. 2007, 129, 11902-11903.
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-
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47
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41549100591
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3 in Negishi cross-couplings, see: (a) Ilies, L.; Tsuji, H.; Sato, Y.; Nakamura, E. Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of (o-Alkynylphenyl)silane. J. Am. Chem. Soc. 2008, 130, 4240-4241.
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3 in Negishi cross-couplings, see: (a) Ilies, L.; Tsuji, H.; Sato, Y.; Nakamura, E. Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of (o-Alkynylphenyl)silane. J. Am. Chem. Soc. 2008, 130, 4240-4241.
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-
-
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48
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33645410710
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Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-y. Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine. J. Am. Chem. Soc. 2006, 128, 3538-3539.
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(b) Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-y. Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine. J. Am. Chem. Soc. 2006, 128, 3538-3539.
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49
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4644349037
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Cross-Coupling of Organyl Halides with Alkenes: The Heck Reaction
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