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0001518849
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When activated aryl halides including fluorides, chlorides, bromides, and iodides were used as substrates, the uncatalyzed coupling of nitriles focused only on phenylacetonitrile derivatives and cyanoacetates as reactants: a) M. Makosza, M. Jagusztyn-Grochowska, M. Ludwikow, M. Jawdosiuk, Tetrahedron 1974, 30, 3723-3735;
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For unactivated aryl fluorides, limitations were encountered on the structures of the nitriles found suitable for reaction. For example, only the anions of secondary nitriles underwent substitution, and ethyl cyanoacetate and primary nitriles were unreactive: S. Caron, E. Vazquez, J. M. Wojcik, J. Am. Chem. Soc. 2000, 122, 712-713.
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26
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0242275771
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note
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Aldrich and Fluka for 1a, 1b, 1c; Strem for 1b.
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28
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33845554248
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For discussions of the electronic structure of tris(alkylamino)-phosphanes, see: a) A. H. Cowley, M. Lattman, P. M. Stricklen, J. G. Verkade, Inorg. Chem. 1982, 21, 543-549;
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Cowley, A.H.1
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0001157766
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34
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84974742301
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3 nitrogen center is rather planar, the sum of angles being 354.9, 356.6, and 357.5°: A. E. Wroblewski, J. Pinkas, J. G. Verkade, Main Group Chem. 1995, 1, 69-79.
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0037010743
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38
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0242275768
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note
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4, filtered, concentrated in vacuo, and purified by column chromatography on silica gel eluting with ethl acetate/hexane or dichloromethane/hexane.
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39
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0242339186
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note
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Control experiments showed that either in the absence of a Pd source or in the absence of proazaphosphatrane, no reaction was observed.
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-
-
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40
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0242275770
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note
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3, no reaction was observed.
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41
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0242339187
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note
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A 1:2 palladium-to-ligand ratio gave faster reaction rates and better product yields than a 1:1 ratio.
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42
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0028200031
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a) C. Cativiela, M. D. Diaz-de-Villegas, J. A. Galvez, J. Org. Chem. 1994, 59, 2497-2505;
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Cativiela, C.1
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Galvez, J.A.3
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