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Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.:, E. Negishi,), Wiley, Hoboken, NJ, 2002
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Metal-Catalyzed Cross-Coupling Reactions
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9
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Metal-catalyzed C-H arylations
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Metal-catalyzed C-H arylations
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Carbonyl α-arylations
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Carbonyl α-arylations
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references cited therein
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Angew. Chem. Int. Ed. 2008, 47, 2127, and references cited therein.
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Angew. Chem. Int. Ed.
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34247537463
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Decarboxylative couplings
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Decarboxylative couplings:, L. J. Goossen, N. Rodríguez, B. Melzer, C. Linder, G. Deng, L. M. Levy, J. Am. Chem. Soc. 2007, 129, 4824.
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78650350556
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For related Pd-catalyzed processes based on diazo compounds, see
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For related Pd-catalyzed processes based on diazo compounds, see
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27
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0035844718
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K. L. Greenman, D. S. Carter, D. L. Van Vranken, Tetrahedron 2001, 57, 5219
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37
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78650332293
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The coupling reaction with hydrazones derived from less substituted acyclic α,β-unsaturated ketones, such as benzylideneacetone, gives rise, under optimized reaction conditions, to a 57: 43 mixture of the expected diene and the pyrazole that is formed by decomposition of the tosylhydrazone followed by electrocyclic ring closure
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The coupling reaction with hydrazones derived from less substituted acyclic α,β-unsaturated ketones, such as benzylideneacetone, gives rise, under optimized reaction conditions, to a 57: 43 mixture of the expected diene and the pyrazole that is formed by decomposition of the tosylhydrazone followed by electrocyclic ring closure.
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38
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77956570131
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The Pd-catalyzed synthesis of tetrasubstituted olefins by the reaction of tosylhydrazones with aryl halides has been recently published under slightly different reaction conditions:,. Nevertheless, we have observed that our protocol can be also employed for the preparation of simple tetrasubstituted alkenes
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The Pd-catalyzed synthesis of tetrasubstituted olefins by the reaction of tosylhydrazones with aryl halides has been recently published under slightly different reaction conditions:, E. Brachet, A. Hamze, J.-F. Peyrat, J.-D. Brion, M. Alami, Org. Lett. 2010, 12, 4042. Nevertheless, we have observed that our protocol can be also employed for the preparation of simple tetrasubstituted alkenes.
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Org. Lett.
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Brachet, E.1
Hamze, A.2
Peyrat, J.-F.3
Brion, J.-D.4
Alami, M.5
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39
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78650381568
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-1 (ΔG) more stable than the TS of the β-hydride elimination from IV, that leads to the cross-conjugated diene. A very large energy difference may justify the exclusive formation of the linear dienes (see Supporting Information for details)
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-1 (ΔG) more stable than the TS of the β-hydride elimination from IV, that leads to the cross-conjugated diene. A very large energy difference may justify the exclusive formation of the linear dienes (see Supporting Information for details).
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40
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78650407904
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For some leading references regarding hydride eliminations on π-allylpalladium complexes see
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For some leading references regarding hydride eliminations on π-allylpalladium complexes see
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41
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33749868637
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in:, (Ed.: E. Negishi), Wiley, Hoboken, NJ, p
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I. Shimizu, in: Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.:, E. Negishi,), Wiley, Hoboken, NJ, 2002, p 1981
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(2002)
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Shimizu, I.1
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J. M. Takacs, E. C. Lawson, F. Clement, J. Am. Chem. Soc. 1997, 119, 5956.
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44
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78650382640
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The reaction with the hydrazone of 3-phenylpropanal led to a 10: 1 mixture of the dienes derived from β-hydride elimination and the vinylogous hydride elimination, respectively
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The reaction with the hydrazone of 3-phenylpropanal led to a 10: 1 mixture of the dienes derived from β-hydride elimination and the vinylogous hydride elimination, respectively.
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