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3
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67649255924
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Schlosser M. (Ed), Wiley, Chichester (chap. 5)
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Hegedus L.S. In: Schlosser M. (Ed). Organometallics in Synthesis (1994), Wiley, Chichester (chap. 5)
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Organometallics in Synthesis
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Hegedus, L.S.1
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6
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0004127624
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Plenum Press, New York
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Colquhoun H.M., Thompson D.J., and Twigg M.V. Carbonylation, Direct Synthesis of Carbonyl Compounds (1991), Plenum Press, New York
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Carbonylation, Direct Synthesis of Carbonyl Compounds
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Colquhoun, H.M.1
Thompson, D.J.2
Twigg, M.V.3
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10
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0000258045
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The low reactivity of aryl chlorides in palladium-catalyzed coupling reactions is generally ascribed to their reluctance to undergo oxidative addition to the catalytically active Pd(0) species. The oxidative addition step is accelerated if electron-deficient aryl chlorides are employed and/or the electron density at the Pd(0) metal center is increased, e.g. by the use of basic phosphine ligands. For an excellent recent review see:. Murai S. (Ed), Springer, Berlin
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The low reactivity of aryl chlorides in palladium-catalyzed coupling reactions is generally ascribed to their reluctance to undergo oxidative addition to the catalytically active Pd(0) species. The oxidative addition step is accelerated if electron-deficient aryl chlorides are employed and/or the electron density at the Pd(0) metal center is increased, e.g. by the use of basic phosphine ligands. For an excellent recent review see:. Grushin V.V., and Alper H. In: Murai S. (Ed). Topics in Organometallic Chemistry 3 (1999), Springer, Berlin 193
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Topics in Organometallic Chemistry
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Grushin, V.V.1
Alper, H.2
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Herrmann W.A., Broßmer C., Öfele K., Reisinger C.-P., Priermeier T., Beller M., and Fischer H. Angew. Chem. Int. Ed. Engl. 34 (1995) 1844
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Angew. Chem. Int. Ed. Engl.
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Herrmann, W.A.1
Broßmer, C.2
Öfele, K.3
Reisinger, C.-P.4
Priermeier, T.5
Beller, M.6
Fischer, H.7
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19
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67649262081
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A. Ehrentraut, A. Zapf, M. Beller, Angew. Chem. 112 (2000) 4315; Angew. Chem. Int. Ed. Engl. 39 (2000) 4153.
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A. Ehrentraut, A. Zapf, M. Beller, Angew. Chem. 112 (2000) 4315; Angew. Chem. Int. Ed. Engl. 39 (2000) 4153.
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Bei X., Crevier T., Guram A.S., Jandeleit B., Powers T.S., Turner H.W., Uno T., and Weinberg W.H. Tetrahedron Lett. 40 (1999) 3855
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Tetrahedron Lett.
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Bei, X.1
Crevier, T.2
Guram, A.S.3
Jandeleit, B.4
Powers, T.S.5
Turner, H.W.6
Uno, T.7
Weinberg, W.H.8
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30
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33748233333
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Beller M., Fischer H., Herrmann W.A., Öfele K., and Broßmer C. Angew. Chem. Int. Ed. Engl. 34 (1995) 1848
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(1995)
Angew. Chem. Int. Ed. Engl.
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Beller, M.1
Fischer, H.2
Herrmann, W.A.3
Öfele, K.4
Broßmer, C.5
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31
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0000876608
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For a recent review about palladium carbonyl complexes see: (a) T. A. Stromnova, I. I. Moiseev, Russ. Chem. Rev. 67 (1998) 485;(b) K. Kudo, M. Hidai, Y. Uchida, J. Organomet. Chem. 33 (1971) 393;(c) M. Hidai, K. Kokura, Y. Uchida, J. Organomet. Chem. 52 (1973) 431.
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For a recent review about palladium carbonyl complexes see: (a) T. A. Stromnova, I. I. Moiseev, Russ. Chem. Rev. 67 (1998) 485;(b) K. Kudo, M. Hidai, Y. Uchida, J. Organomet. Chem. 33 (1971) 393;(c) M. Hidai, K. Kokura, Y. Uchida, J. Organomet. Chem. 52 (1973) 431.
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44
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67649243618
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note
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Due to their π-acceptor properties, CO ligands withdraw electron density from the Pd(0) center, thereby hampering the oxidative addition of the aryl chloride substrate.
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46
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0000345787
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Togni A., Breutel C., Schnyder A., Spindler F., Landert H., and Tijani A. J. Am. Chem. Soc. 116 (1994) 4062
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(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 4062
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Togni, A.1
Breutel, C.2
Schnyder, A.3
Spindler, F.4
Landert, H.5
Tijani, A.6
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48
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0001898589
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Togni A. Chimia 50 (1996) 86
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(1996)
Chimia
, vol.50
, pp. 86
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Togni, A.1
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50
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0033450792
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Blaser H.-U., Buser H.P., Coers K., Hanreich R., Jalett H.-P., Jelsch E., Pugin B., Schneider H.-D., Spindler F., and Wegmann A. Chimia 53 (1999) 275
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(1999)
Chimia
, vol.53
, pp. 275
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Blaser, H.-U.1
Buser, H.P.2
Coers, K.3
Hanreich, R.4
Jalett, H.-P.5
Jelsch, E.6
Pugin, B.7
Schneider, H.-D.8
Spindler, F.9
Wegmann, A.10
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53
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67649246727
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Software: statgraphics plus for Windows 3.1.
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Software: statgraphics plus for Windows 3.1.
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54
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67649252968
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note
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A P/Pd ratio of 80 was chosen in this experiment, i.e. the ligand concentration was kept constant at 2 mol%. A former study of carbonylation reactions has shown that, for a given Pd concentration, the phosphine ligand concentration instead of the P/Pd ratio is the relevant parameter.
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55
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67649295357
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note
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A higher TON of 3100 was only reported in an example describing the palladium-catalyzed aminocarbonylation of the strongly activated substrate in 2-position (2,5-dichloropyridine): M. Scalone, P. Vogt, (Hoffmann-La Roche) EP 385 210 A2 (1990); Chem. Abstr. 114 (1991) 143153k.
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56
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67649271392
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note
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2/4 catalyst is more active with electron rich substrates may indicate that the oxidative addition of the aryl chloride is not the rate determining step under the applied conditions.
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58
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24344482675
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Kim T.-J., Kim Y.-H., Kim H.-S., Shim S.-C., Kwak Y.-W., Cha J.-S., Lee H.-S., Uhm J.-K., and Byun S.-I. Bull. Korean Chem. Soc. 13 (1992) 588
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(1992)
Bull. Korean Chem. Soc.
, vol.13
, pp. 588
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Kim, T.-J.1
Kim, Y.-H.2
Kim, H.-S.3
Shim, S.-C.4
Kwak, Y.-W.5
Cha, J.-S.6
Lee, H.-S.7
Uhm, J.-K.8
Byun, S.-I.9
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60
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67649271390
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note
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For experiments at different temperatures, CO pressures, and catalyst concentrations, or with other ligands and bases, the conditions given in the respective tables were used.
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61
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67649292641
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note
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Since the mixture of (4-carboxyphenyl)acetic acid and (4-butoxycarbonylphenyl)acetic acid, as isolated from the respective carbonylation experiment, was not separated, only the NMR data of these by-products is given.
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