-
2
-
-
0000633011
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, Chapter 4.3
-
(b) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol 4, Chapter 4.3, p 833.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 833
-
-
Heck, R.F.1
-
4
-
-
0037782994
-
-
Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany
-
(d) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 99.
-
(1998)
Metal-Catalyzed Cross-Coupling Reactions
, pp. 99
-
-
Bräse, S.1
De Meijere, A.2
-
5
-
-
0001325299
-
-
Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany
-
(e) Beller, M.; Riermeier, T. H.; Stark, G. In Transition Metals for Organic Synthesis; Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol 1, p 208.
-
(1998)
Transition Metals for Organic Synthesis; Building Blocks and Fine Chemicals
, vol.1
, pp. 208
-
-
Beller, M.1
Riermeier, T.H.2
Stark, G.3
-
7
-
-
0035959456
-
-
(g) Whitcombe, N. J.; Hii, K. K. (M.); Gibson, S. E. Tetrahedron 2001, 57, 7449.
-
(2001)
Tetrahedron
, vol.57
, pp. 7449
-
-
Whitcombe, N.J.1
Hii, K.K.2
Gibson, S.E.3
-
9
-
-
0037112673
-
-
Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 4176
-
-
Littke, A.F.1
Fu, G.C.2
-
10
-
-
0032787242
-
-
van Strijdonck, G. P. F.; Boele, M. D. K.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. Eur. J. Inorg. Chem. 1999, 1073.
-
(1999)
Eur. J. Inorg. Chem.
, pp. 1073
-
-
Van Strijdonck, G.P.F.1
Boele, M.D.K.2
Kamer, P.C.J.3
De Vries, J.G.4
Van Leeuwen, P.W.N.M.5
-
11
-
-
0031925015
-
-
(a) Stephan, M. S.; Teunissen, A. J. J. M.; Verzijl, G. K. M.; de Vries, J. G. Angew. Chem., Int. Ed. 1998, 37, 662.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 662
-
-
Stephan, M.S.1
Teunissen, A.J.J.M.2
Verzijl, G.K.M.3
De Vries, J.G.4
-
12
-
-
0141804079
-
-
Ford, M. E., Ed.; Marcel Dekker Inc.: New York
-
(b) Stephan, M. S.; de Vries, J. G. In Chemical Industries 82, Catalysis of Organic Reactions; Ford, M. E., Ed.; Marcel Dekker Inc.: New York, 2000, p 379. For further work on this concept see: Goossen, L. J.; Paetzold, J.; Ghosh, K. Synlett 2002, 1721 and references therein.
-
(2000)
Chemical Industries 82, Catalysis of Organic Reactions
, pp. 379
-
-
Stephan, M.S.1
De Vries, J.G.2
-
13
-
-
84856330915
-
-
and references therein
-
(b) Stephan, M. S.; de Vries, J. G. In Chemical Industries 82, Catalysis of Organic Reactions; Ford, M. E., Ed.; Marcel Dekker Inc.: New York, 2000, p 379. For further work on this concept see: Goossen, L. J.; Paetzold, J.; Ghosh, K. Synlett 2002, 1721 and references therein.
-
(2002)
Synlett
, pp. 1721
-
-
Goossen, L.J.1
Paetzold, J.2
Ghosh, K.3
-
14
-
-
0000629440
-
-
Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT
-
Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1996; Vol 5, p 153. See also: Ziegler, C. B., Jr.; Heck, R. F. J. Org. Chem. 1978, 43, 2941.
-
(1996)
Advances in Metal-Organic Chemistry
, vol.5
, pp. 153
-
-
Jeffery, T.1
-
15
-
-
33947092885
-
-
Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1996; Vol 5, p 153. See also: Ziegler, C. B., Jr.; Heck, R. F. J. Org. Chem. 1978, 43, 2941.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2941
-
-
Ziegler C.B., Jr.1
Heck, R.F.2
-
16
-
-
0141469306
-
-
note
-
The phrase "ligand-free" is used when no additional ligand, e.g., a phosphine, is added to the reaction mixture to keep the palladium in solution.
-
-
-
-
17
-
-
0000514493
-
-
(a) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371, 397.
-
(1989)
J. Organomet. Chem.
, vol.371
, pp. 397
-
-
Bumagin, N.A.1
More, P.G.2
Beletskaya, I.P.3
-
19
-
-
0012356884
-
-
de Vries, A. H. M.; Parlevliet, F. J.; Schmieder-van de Vondervoort, L.; Mommers, J. H. M.; Henderickx, H. J. W.; Walet, M. A. N.; de Vries, J. G. Adv. Synth. Catal. 2002, 344, 996.
-
(2002)
Adv. Synth. Catal.
, vol.344
, pp. 996
-
-
De Vries, A.H.M.1
Parlevliet, F.J.2
Schmieder-van De Vondervoort, L.3
Mommers, J.H.M.4
Henderickx, H.J.W.5
Walet, M.A.N.6
De Vries, J.G.7
-
20
-
-
0141804080
-
-
note
-
Although aryl chlorides are cheaper than aryl bromides, the TON numbers attained for aryl chlorides are much lower than those for aryl bromides, so overall, a process based on an aryl bromide with low-loading palladium is cheaper. See also the concluding paragraph in ref 3.
-
-
-
-
22
-
-
0030600195
-
-
(a) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 4499
-
-
Reetz, M.T.1
Breinbauer, R.2
Wanninger, K.3
-
23
-
-
0030576421
-
-
(b) Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C.-P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257.
-
(1996)
J. Organomet. Chem.
, vol.520
, pp. 257
-
-
Beller, M.1
Fischer, H.2
Kühlein, K.3
Reisinger, C.-P.4
Herrmann, W.A.5
-
24
-
-
0034598519
-
-
(c) Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 165
-
-
Reetz, M.T.1
Westermann, E.2
-
25
-
-
0030694572
-
-
(a) Klingelhöfer, S.; Heitz, W.; Greiner, A.; Oestreich, S.; Förster, S.; Antonietti, M. J. Am. Chem. Soc. 1997, 119, 10116.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 10116
-
-
Klingelhöfer, S.1
Heitz, W.2
Greiner, A.3
Oestreich, S.4
Förster, S.5
Antonietti, M.6
-
26
-
-
0037161724
-
-
(b) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134.
-
(2002)
Chem. Commun.
, pp. 1134
-
-
Ley, S.V.1
Ramarao, C.2
Gordon, R.S.3
Holmes, A.B.4
Morrison, A.J.5
McConvey, I.F.6
Shirley, I.M.7
Smith, S.C.8
Smith, M.D.9
-
27
-
-
0037739323
-
-
(c) Bergbreiter, D. E.; Osburn, P. L.; Li, C. Org. Lett. 2002, 4, 737.
-
(2002)
Org. Lett.
, vol.4
, pp. 737
-
-
Bergbreiter, D.E.1
Osburn, P.L.2
Li, C.3
-
28
-
-
0001150340
-
-
Rahim, E. H.; Kamounah, F. S.; Frederiksen, J.; Christense, J. B. Nano Lett. 2001, 1, 499-501.
-
(2001)
Nano Lett.
, vol.1
, pp. 499-501
-
-
Rahim, E.H.1
Kamounah, F.S.2
Frederiksen, J.3
Christense, J.B.4
-
29
-
-
0012718418
-
-
Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529.
-
(2002)
Org. Lett.
, vol.4
, pp. 3529
-
-
Kogan, V.1
Aizenshtat, Z.2
Popovitz-Biro, R.3
Neumann, R.4
-
32
-
-
0141692498
-
-
note
-
The low loading of ligand-free palladium (in our examples 0.01-0.1 mol %) has been dubbed as homeopathic doses, a phrase also used by Beletskaya and Cheprakov, see ref 1f, p 3009.
-
-
-
-
33
-
-
0032511940
-
-
2 at 0.009 mol % sufficing for 77% conversion after 24 h. Reetz, M. T.; Westermann, E.; Lohmer, R.; Lohmer, G. Tetrahedron Lett. 1998, 39, 8449.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 8449
-
-
Reetz, M.T.1
Westermann, E.2
Lohmer, R.3
Lohmer, G.4
-
34
-
-
0141580946
-
-
note
-
-1.
-
-
-
-
35
-
-
0000740923
-
-
A mixture of a β-trans- and β-cis-arylated product was found, see also: Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1987, 52, 3529.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 3529
-
-
Andersson, C.-M.1
Hallberg, A.2
-
36
-
-
33750236967
-
-
(a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 1844
-
-
Herrmann, W.A.1
Brossmer, C.2
Öfele, K.3
Reisinger, C.-P.4
Priermeier, T.5
Beller, M.6
Fischer, H.7
-
37
-
-
0030767352
-
-
(b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357.
-
(1997)
Chem. Eur. J.
, vol.3
, pp. 1357
-
-
Herrmann, W.A.1
Brossmer, C.2
Reisinger, C.-P.3
Riermeier, T.H.4
Öfele, K.5
Beller, M.6
-
39
-
-
0141469305
-
-
note
-
The observed TOF values for the palladacycle in NMP correspond nicely with the ones reported in DMF, see ref 22.
-
-
-
-
40
-
-
0034619245
-
-
Nowotny, M.; Hanefeld, U.; van Koningsfeld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877.
-
(2000)
Chem. Commun.
, pp. 1877
-
-
Nowotny, M.1
Hanefeld, U.2
Van Koningsfeld, H.3
Maschmeyer, T.4
-
43
-
-
0001841732
-
-
Beletskaya, I. P.; Kashin, A. N.; Karlstedt, N. B.; Mitin, A. V.; Cheprakov, A. V.; Kazankov, G. M. J. Organomet. Chem. 2001, 622, 89.
-
(2001)
J. Organomet. Chem.
, vol.622
, pp. 89
-
-
Beletskaya, I.P.1
Kashin, A.N.2
Karlstedt, N.B.3
Mitin, A.V.4
Cheprakov, A.V.5
Kazankov, G.M.6
-
44
-
-
0032564547
-
-
(a) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 9793
-
-
Albisson, D.A.1
Bedford, R.B.2
Scully, P.N.3
-
45
-
-
19044389954
-
-
(b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172.
-
(2002)
Adv. Synth. Catal.
, vol.344
, pp. 172
-
-
Alonso, D.A.1
Nájera, C.2
Pacheco, M.C.3
-
46
-
-
0001703882
-
-
(c) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287.
-
(2000)
Org. Lett.
, vol.2
, pp. 1287
-
-
Gruber, A.S.1
Zim, D.2
Ebeling, G.3
Monteiro, A.L.4
Dupont, J.5
-
48
-
-
0035926108
-
-
(e) Gibson, S.; Foster, D. F.; Eastham, G. R.; Tooze, R. P.; Cole-Hamilton, D. J. Chem. Commun. 2001, 779.
-
(2001)
J. Chem. Commun.
, pp. 779
-
-
Gibson, S.1
Foster, D.F.2
Eastham, G.R.3
Tooze, R.P.4
Cole-Hamilton, D.5
-
49
-
-
0035820028
-
-
Pfaltz and Blackmond, in their study on the kinetics of a Heck reaction catalyzed by a palladacycle, assumed that this phenomenon is due to a preequilibrium between a dimeric and a monomeric aryl-Pd(II) species. They found half-order in [Pd]. See: Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848. For the cluster case an order between 0 and 1 is expected.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 1848
-
-
Rosner, T.1
Le Bars, J.2
Pfaltz, A.3
Blackmond, D.G.4
-
51
-
-
0036013817
-
-
Evans, J.; O'Neill, L.; Kambhampati, V. L.; Rayner, G.; Turin, S.; Genge, A.; Dent, A. J.; Neisius, T. J. Chem. Soc., Dalton Trans. 2002, 2207.
-
(2002)
J. Chem. Soc., Dalton Trans.
, pp. 2207
-
-
Evans, J.1
O'Neill, L.2
Kambhampati, V.L.3
Rayner, G.4
Turin, S.5
Genge, A.6
Dent, A.J.7
Neisius, T.8
-
52
-
-
0141630304
-
-
The actual mechanism is currently a subject of study. Very recently a palladacycle was proposed as a reservoir of an active Pd(0) species, see: Consorti, C. S.; Zanini, M. L.; Leal, S.; Ebeling, G.; Dupont, J. Org. Lett. 2003, 5, 983.
-
(2003)
Org. Lett.
, vol.5
, pp. 983
-
-
Consorti, C.S.1
Zanini, M.L.2
Leal, S.3
Ebeling, G.4
Dupont, J.5
-
53
-
-
0032477347
-
-
Mehnert, C. P.; Weaver, D. W.; Ying, J. Y. J. Am. Chem. Soc. 1998, 120, 12289.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 12289
-
-
Mehnert, C.P.1
Weaver, D.W.2
Ying, J.Y.3
-
55
-
-
0037184451
-
-
and references therein
-
Choudary, B.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127 and references therein.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 14127
-
-
Choudary, B.1
Madhi, S.2
Chowdari, N.S.3
Kantam, M.L.4
Sreedhar, B.5
-
56
-
-
0037010004
-
-
Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11572
-
-
Mori, K.1
Yamaguchi, K.2
Hara, T.3
Mizugaki, T.4
Ebitani, K.5
Kaneda, K.6
-
58
-
-
0035904434
-
-
(b) Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 10139
-
-
Davies, I.W.1
Matty, L.2
Hughes, D.L.3
Reider, P.J.4
-
59
-
-
0037006237
-
-
(c) Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622.
-
(2002)
Chem. Eur. J.
, vol.8
, pp. 622
-
-
Köhler, K.1
Heidenreich, R.G.2
Krauter, J.G.E.3
Pietsch, J.4
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