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The names of these reactions were adopted from the book written by Tsuji, although some names are not often referred to Tsuji, J. Transition Metal Reagents and Catalysts, Innovations in Organic Synthesis; John Wiley: Chichester, 2000.
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The names of these reactions were adopted from the book written by Tsuji, although some names are not often referred to Tsuji, J. Transition Metal Reagents and Catalysts, Innovations in Organic Synthesis; John Wiley: Chichester, 2000.
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28
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0037021032
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Recent breakthroughs reported by some groups in the transition metal-catalyzed coupling reactions for the C C bond-formation between unactivated sp3-carbons of the substrates should be noted. Pd: (a) Frisch, A.C, Shaikh, N, Zapf, A, Beller, M. Angew. Chem, Int. Ed. 2002, 41, 4056;
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The oxidative addition by retention is also reported: Farthing, C.N.; Kocovsky, P. J. Am. Chem. Soc.. 1998, 120, 6661, and references therein.
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The oxidative addition by retention is also reported: Farthing, C.N.; Kocovsky, P. J. Am. Chem. Soc.. 1998, 120, 6661, and references therein.
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36
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46149113166
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The reductive elimination using hard nucleophiles such as Griganard reagents generally proceeds by retention via transmetallation
-
The reductive elimination using hard nucleophiles such as Griganard reagents generally proceeds by retention via transmetallation.
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46149110242
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3: tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct.
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3: tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct.
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59
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46149112940
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1,2-bis(diphenylphosphino)ethane
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Dppe1
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60
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46149106530
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SEC: size exclusion chromatography
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SEC: size exclusion chromatography.
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61
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46149092123
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3: tricyclohexylphosphine.
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3: tricyclohexylphosphine.
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62
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46149084601
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1,4-bis(diphenylphosphino)butane
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Dppb1
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63
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46149127042
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The original mechanism was slightly modified according to the general grounds of π-allylpalladium chemistry. The soft nucleophile directly attacks the allylic terminal carbon of the π-allylpalladium complex
-
The original mechanism was slightly modified according to the general grounds of π-allylpalladium chemistry. The soft nucleophile directly attacks the allylic terminal carbon of the π-allylpalladium complex.
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Although the oxidative addition of allylic carbonate to Pd(0) had been assumed as an irreversible reaction, it could be reversible. Amatore, C, Gamez, S, Jutand, A, Meyer, G, Moreno-Mañas, M, Morral, L, Pleixats, R. Chem.-Eur. J. 2000, 6, 3372
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Although the oxidative addition of allylic carbonate to Pd(0) had been assumed as an irreversible reaction, it could be reversible. Amatore, C.; Gamez, S.; Jutand, A.; Meyer, G.; Moreno-Mañas, M.; Morral, L.; Pleixats, R. Chem.-Eur. J. 2000, 6, 3372.
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Recently, the high efficiency of zinc alkoxides for the formation of C-O bonds via the π-allylpalladium complex reported in ref 37 has been acknowledged in organic synthesis. See ref 36b.
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One of the examples: Boardman, F.H.; Grice, A.W.; Rüther, M.G.; Sheldon, T.J.; Bradley, D.D.C.; Burn, P.L. Macromolecules 1999, 32, 111.
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46149109418
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91
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46149103834
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1,3-bis(diphenylphosphino)propane
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Dppp1
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92
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46149090520
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1,1′-bis(diphenylphosphino)ferrocene
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it was slower than dppb. Other ligands gave only oligomers
-
Dppf: 1,1′-bis(diphenylphosphino)ferrocene. Although dppf also promoted the polycondensation reaction, it was slower than dppb. Other ligands gave only oligomers.
-
Although dppf also promoted the polycondensation reaction
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Dppf1
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93
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46149106303
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2 of the main chain).
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2 of the main chain).
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94
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0006277518
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The details of this principle will be discussed in the next section
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Flory, J.P. Chem. Rev. 1946, 39, 137. The details of this principle will be discussed in the next section.
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At the same time when our paper ref, 55a, was published, Hay reported the polycondensation under the imbalanced conditions, while the system was rather heterogeneous: Miyatake, K, Hlil, A.R, Hay, A.S. Macromolecules 2001, 34, 4288
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At the same time when our paper (ref. [55a]) was published, Hay reported the polycondensation under the imbalanced conditions, while the system was rather heterogeneous: Miyatake, K.; Hlil, A.R.; Hay, A.S. Macromolecules 2001, 34, 4288.
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A related C-S bond-forming polycondensation was also reported: Iimori, H.; Shibasaki, Y.; Ando, S.; Ueda, M. Macromol. Symp. 2003, 199, 23.
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During the preparation of this manuscript, Moore reported another intriguing approach of homogeneous two-component polycondensation via nucleation-elongation under imbalanced stoichiometry: Zhao, D.; Moore, J. S. J. Am. Chem. Soc. 2003, 125, 16294.
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