-
1
-
-
0000259867
-
-
(a) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.-i.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
-
(1976)
Bull. Chem. Soc. Jpn.
, vol.49
, pp. 1958
-
-
Tamao, K.1
Sumitani, K.2
Kiso, Y.3
Zembayashi, M.4
Fujioka, A.5
Kodama, S.-I.6
Nakajima, I.7
Minato, A.8
Kumada, M.9
-
4
-
-
0000976664
-
-
For recent nickel-catalyzed Kumada couplings using polymerimmobilized catalysts, see: Styring, P.; Grindon, C.; Fisher, C. M. Catal. Lett. 2001, 77, 219.
-
(2001)
Catal. Lett.
, vol.77
, pp. 219
-
-
Styring, P.1
Grindon, C.2
Fisher, C.M.3
-
5
-
-
0001038733
-
-
(a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
-
(1998)
Acc. Chem. Res.
, vol.31
, pp. 805
-
-
Wolfe, J.P.1
Wagaw, S.2
Marcoux, J.-F.3
Buchwald, S.L.4
-
8
-
-
0000897978
-
-
Hartwig, J. F. Angew. Chem. 1998, 110, 2154-2177; Angew. Chem., Int. Ed. 1998, 37, 2046.
-
(1998)
Angew. Chem.
, vol.110
, pp. 2154-2177
-
-
Hartwig, J.F.1
-
9
-
-
0032541260
-
-
Hartwig, J. F. Angew. Chem. 1998, 110, 2154-2177; Angew. Chem., Int. Ed. 1998, 37, 2046.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 2046
-
-
-
10
-
-
0037060980
-
-
Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
-
(2002)
Tetrahedron
, vol.58
, pp. 2041
-
-
Prim, D.1
Campagne, J.-M.2
Joseph, D.3
Andrioletti, B.4
-
11
-
-
0003638901
-
-
McGraw-Hill: New York
-
The oxidation potential for the system Pd(II)/Pd(0) is much higher than that of Ni(II)/Ni(0), therefore Ni(0) is more prone to oxidative addition; Dean, J. A. Lange's Handbook of Chemistry, 14th ed.; McGraw-Hill: New York, 1992.
-
(1992)
Lange's Handbook of Chemistry, 14th Ed.
-
-
Dean, J.A.1
-
13
-
-
0003690482
-
-
D. Reidel Publishing Company: Boston
-
The bond strength for nickel halides increases from iodine to chlorine, whereas those for palladium halides decreases in that order. Therefore, the energy gain from the formed metal-halide bond during oxidative addition is highest for Ni-Cl but lowest for Pd-Cl. See ref 7 and Henry, P. M. Palladium Catalyzed Oxidation of Hydrocarbons; D. Reidel Publishing Company: Boston, 1980; pp 11-12.
-
(1980)
Palladium Catalyzed Oxidation of Hydrocarbons
, pp. 11-12
-
-
Henry, P.M.1
-
14
-
-
33748731943
-
-
(a) Shirakawa, E.; Yamasaki, K.; Hiyama, T. J. Chem. Soc., Perkin Trans. 1 1997, 2449.
-
(1997)
J. Chem. Soc., Perkin Trans. 1
, pp. 2449
-
-
Shirakawa, E.1
Yamasaki, K.2
Hiyama, T.3
-
15
-
-
0000728442
-
-
(b) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 8024
-
-
Saito, S.1
Oh-tani, S.2
Miyaura, N.3
-
17
-
-
0025328473
-
-
and references therein
-
(d) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80, and references therein.
-
(1990)
Bull. Chem. Soc. Jpn.
, vol.63
, pp. 80
-
-
Iyoda, M.1
Otsuka, H.2
Sato, K.3
Nisato, N.4
Oda, M.5
-
19
-
-
0037012946
-
-
and references therein
-
Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029; and references therein.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3029
-
-
Desmarets, C.1
Schneider, R.2
Fort, Y.3
-
21
-
-
0013372359
-
-
and references therein
-
Lipshutz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. J. Org. Chem. 2002, 67, 1177, and references therein.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 1177
-
-
Lipshutz, B.H.1
Tasler, S.2
Chrisman, W.3
Spliethoff, B.4
Tesche, B.5
-
22
-
-
0001320798
-
-
(a) Stürmer, R. Angew. Chem. 1999, 111, 3509; Angew. Chem., Int. Ed. 1999, 38, 3307, and references therein.
-
(1999)
Angew. Chem.
, vol.111
, pp. 3509
-
-
Stürmer, R.1
-
23
-
-
0039097693
-
-
and references therein
-
(a) Stürmer, R. Angew. Chem. 1999, 111, 3509; Angew. Chem., Int. Ed. 1999, 38, 3307, and references therein.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 3307
-
-
-
27
-
-
33750236967
-
-
(e) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 107, 1989; Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
-
(1995)
Angew. Chem.
, vol.107
, pp. 1989
-
-
Herrmann, W.A.1
Brossmer, C.2
Öfele, K.3
Reisinger, C.-P.4
Priermeier, T.5
Beller, M.6
Fischer, H.7
-
28
-
-
33750236967
-
-
(e) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 107, 1989; Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 1844
-
-
-
29
-
-
33748233333
-
-
(f) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem. 1995, 107, 1992; Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
-
(1995)
Angew. Chem.
, vol.107
, pp. 1992
-
-
Beller, M.1
Fischer, H.2
Herrmann, W.A.3
Öfele, K.4
Brossmer, C.5
-
30
-
-
33748233333
-
-
(f) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem. 1995, 107, 1992; Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 1848
-
-
-
31
-
-
0032747809
-
-
(g) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 9550
-
-
Wolfe, J.P.1
Singer, R.A.2
Yang, B.H.3
Buchwald, S.L.4
-
32
-
-
0034698329
-
-
(h) Mathews, C. J.; Smith, P. J.; Welton, T. J. Chem. Soc., Chem. Commun. 2000, 1249.
-
(2000)
J. Chem. Soc., Chem. Commun.
, pp. 1249
-
-
Mathews, C.J.1
Smith, P.J.2
Welton, T.3
-
33
-
-
0034700606
-
-
(i) Andreu, M. G.; Zapf, A.; Beller, M. J. Chem. Soc., Chem. Commun. 2000, 2475.
-
(2000)
J. Chem. Soc., Chem. Commun.
, pp. 2475
-
-
Andreu, M.G.1
Zapf, A.2
Beller, M.3
-
35
-
-
0027578277
-
-
(k) Carpentier, J. F.; Petit, F.; Mortreux, A.; Dufaud, V.; Basset, J.-M.; Thivolle-Cazat, J. J. Mol. Catal. 1993, 81, 1.
-
(1993)
J. Mol. Catal.
, vol.81
, pp. 1
-
-
Carpentier, J.F.1
Petit, F.2
Mortreux, A.3
Dufaud, V.4
Basset, J.-M.5
Thivolle-Cazat, J.6
-
37
-
-
0013372040
-
-
Hughes, E. C.; Veatch, F.; Elersich, V. Ind. Eng. Chem. 1950, 42, 787.
-
(1950)
Ind. Eng. Chem.
, vol.42
, pp. 787
-
-
Hughes, E.C.1
Veatch, F.2
Elersich, V.3
-
39
-
-
0001100670
-
-
Lipshutz, B. H.; Ueda, H. Angew. Chem. 2000, 112, 4666; Angew. Chem., Int. Ed. 2000, 39, 4492.
-
(2000)
Angew. Chem.
, vol.112
, pp. 4666
-
-
Lipshutz, B.H.1
Ueda, H.2
-
40
-
-
0034671512
-
-
Lipshutz, B. H.; Ueda, H. Angew. Chem. 2000, 112, 4666; Angew. Chem., Int. Ed. 2000, 39, 4492.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 4492
-
-
-
41
-
-
0001049359
-
-
Lipshutz, B. H.; Tomioka, T.; Blomgren, P. A.; Sclafani, J. A. Inorg. Chim. Acta 1999, 296, 164.
-
(1999)
Inorg. Chim. Acta
, vol.296
, pp. 164
-
-
Lipshutz, B.H.1
Tomioka, T.2
Blomgren, P.A.3
Sclafani, J.A.4
-
44
-
-
0000852316
-
-
(c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
-
(1992)
Organometallics
, vol.11
, pp. 3009
-
-
Amatore, C.1
Jutand, A.2
M'Barki, M.A.3
-
48
-
-
0032532256
-
-
Park, M.; Buck, J. R.; Rizzo, C. J. Tetrahedron 1998, 54, 12707.
-
(1998)
Tetrahedron
, vol.54
, pp. 12707
-
-
Park, M.1
Buck, J.R.2
Rizzo, C.J.3
-
49
-
-
0344923845
-
-
Sofia, A.; Karlström, E.; Itami, K.; Bäckvall, J. E. J. Org. Chem. 1999, 64, 1745.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1745
-
-
Sofia, A.1
Karlström, E.2
Itami, K.3
Bäckvall, J.E.4
-
50
-
-
0013326375
-
-
note
-
3 was also unsuitable for these aromatic aminations.
-
-
-
-
51
-
-
0013376450
-
-
note
-
14
-
-
-
-
53
-
-
84970606098
-
-
For a similar reduction of Pd(II) by tertiary amines, see: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res. (S) 1984, 360. (b) Beckwith, A. L. J.; Eichinger, P. H.; Mooney, B. A.; Prager, R. H. Aust. J. Chem. 1983, 36, 719.
-
(1984)
J. Chem. Res. (S)
, pp. 360
-
-
McCrindle, R.1
Ferguson, G.2
Arsenault, G.J.3
McAlees, A.J.4
Stephenson, D.K.5
-
54
-
-
84970606098
-
-
For a similar reduction of Pd(II) by tertiary amines, see: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res. (S) 1984, 360. (b) Beckwith, A. L. J.; Eichinger, P. H.; Mooney, B. A.; Prager, R. H. Aust. J. Chem. 1983, 36, 719.
-
(1983)
Aust. J. Chem.
, vol.36
, pp. 719
-
-
Beckwith, A.L.J.1
Eichinger, P.H.2
Mooney, B.A.3
Prager, R.H.4
-
55
-
-
0013376451
-
-
note
-
For experimental details, see Supporting Information.
-
-
-
-
56
-
-
0000396165
-
-
Formation of palladium colloids was postulated to generate reactive species in ligandless Heck reactions and homocoupling of chlorobenzene; see: (a) Reetz, M. T.; Westermann, E. Angew. Chem. 2000, 112, 170; Angew. Chem., Int. Ed. 2000, 39, 165. (b) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Sasson, Y. J. Org. Chem. 2000, 65, 3107.
-
(2000)
Angew. Chem.
, vol.112
, pp. 170
-
-
Reetz, M.T.1
Westermann, E.2
-
57
-
-
0034598519
-
-
Formation of palladium colloids was postulated to generate reactive species in ligandless Heck reactions and homocoupling of chlorobenzene; see: (a) Reetz, M. T.; Westermann, E. Angew. Chem. 2000, 112, 170; Angew. Chem., Int. Ed. 2000, 39, 165. (b) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Sasson, Y. J. Org. Chem. 2000, 65, 3107.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 165
-
-
-
58
-
-
0034685862
-
-
Formation of palladium colloids was postulated to generate reactive species in ligandless Heck reactions and homocoupling of chlorobenzene; see: (a) Reetz, M. T.; Westermann, E. Angew. Chem. 2000, 112, 170; Angew. Chem., Int. Ed. 2000, 39, 165. (b) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Sasson, Y. J. Org. Chem. 2000, 65, 3107.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3107
-
-
Mukhopadhyay, S.1
Rothenberg, G.2
Gitis, D.3
Sasson, Y.4
-
59
-
-
0001594899
-
-
Vol'pin, M. E.; Novikov, Y. N.; Lapkina, N. D.; Kasatochkin, V. I.; Struchkov, Y. T.; Kazakov, M. E.; Stukan, R. A.; Povitskij, V. A.; Karimov, Y. S.; Zvarikina, A. V. J. Am. Chem. Soc. 1975, 97, 3366.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 3366
-
-
Vol'pin, M.E.1
Novikov, Y.N.2
Lapkina, N.D.3
Kasatochkin, V.I.4
Struchkov, Y.T.5
Kazakov, M.E.6
Stukan, R.A.7
Povitskij, V.A.8
Karimov, Y.S.9
Zvarikina, A.V.10
-
60
-
-
0013424463
-
-
note
-
Kumada couplings displayed higher levels of conversion even with electron-rich aryl chlorides (i.e., deactivated for oxidative addition) in the same reaction times as aromatic aminations (albeit in different solvents, THF vs toluene). Hence, oxidative addition is not likely to be rate-limiting.
-
-
-
-
61
-
-
0001275795
-
-
That different mechanistic pathways are operating for reductive elimination with different ligands cannot be ruled out; e.g., triggering of reductive elimination by SET: (a) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1978, 100, 1634. (b) Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262. (c) Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421. See also ref 40.
-
(1978)
J. Am. Chem. Soc.
, vol.100
, pp. 1634
-
-
Tsou, T.T.1
Kochi, J.K.2
-
62
-
-
33847802803
-
-
That different mechanistic pathways are operating for reductive elimination with different ligands cannot be ruled out; e.g., triggering of reductive elimination by SET: (a) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1978, 100, 1634. (b) Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262. (c) Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421. See also ref 40.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 7262
-
-
Morrell, D.G.1
Kochi, J.K.2
-
63
-
-
0001038041
-
-
See also ref 40
-
That different mechanistic pathways are operating for reductive elimination with different ligands cannot be ruled out; e.g., triggering of reductive elimination by SET: (a) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1978, 100, 1634. (b) Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262. (c) Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421. See also ref 40.
-
(1995)
Organometallics
, vol.14
, pp. 4421
-
-
Koo, K.1
Hillhouse, G.L.2
-
64
-
-
33751155220
-
-
(a) Segelstein, B. E.; Butler, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 12
-
-
Segelstein, B.E.1
Butler, T.W.2
Chenard, B.L.3
-
65
-
-
0031585711
-
-
(b) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 12441
-
-
Goodson, F.E.1
Wallow, T.I.2
Novak, B.M.3
-
67
-
-
0034707379
-
-
(d) Kwong, F. Y.; Lai, C. W.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 10285.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 10285
-
-
Kwong, F.Y.1
Lai, C.W.2
Tian, Y.3
Chan, K.S.4
-
70
-
-
0001262616
-
-
(a) Amatore, C.; Jutand, A.; Mottier, L. J. Electroanal. Chem. 1991, 306, 125.
-
(1991)
J. Electroanal. Chem.
, vol.306
, pp. 125
-
-
Amatore, C.1
Jutand, A.2
Mottier, L.3
-
72
-
-
0001285340
-
-
Percec, V.; Bae, J.-Y.; Zhao, M.; Hill, D. H. J. Org. Chem. 1995, 60, 176.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 176
-
-
Percec, V.1
Bae, J.-Y.2
Zhao, M.3
Hill, D.H.4
-
73
-
-
0034552449
-
-
(a) Amatore, C.; Jutand, A.; Perichon, J.; Rollin, Y. Monatsh. Chem. 2000, 131, 1293.
-
(2000)
Monatsh. Chem.
, vol.131
, pp. 1293
-
-
Amatore, C.1
Jutand, A.2
Perichon, J.3
Rollin, Y.4
-
75
-
-
0000785505
-
-
(a) Carloni, P.; Greci, L.; Stipa, P.; Eberson, L. J. Org. Chem. 1991, 56, 4733.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4733
-
-
Carloni, P.1
Greci, L.2
Stipa, P.3
Eberson, L.4
-
76
-
-
0029873218
-
-
(b) Bruni, P.; Carloni, P.; Conti, C.; Giorgini, E.; Greci, L.; Iacussi, M.; Stipa, P.; Tosi, G. Tetrahedron 1996, 52, 6795.
-
(1996)
Tetrahedron
, vol.52
, pp. 6795
-
-
Bruni, P.1
Carloni, P.2
Conti, C.3
Giorgini, E.4
Greci, L.5
Iacussi, M.6
Stipa, P.7
Tosi, G.8
-
78
-
-
0013370295
-
-
For further examples of cross-coupling reactions of aryl halides with only aromatic Grignard reagents catalyzed by nonligated nickel, see: (a) Ikoma, Y.; Taya, F.; Ozaki, E.-i.; Higuchi, S.; Naoi, Y.; Fuji-i, K. Synthesis 1990, 147. (b) Ikoma, Y.; Ando, K.; Naoi, Y.; Akiyama, T.; Sugimori, A. Synth. Commun. 1991, 21, 481.
-
(1990)
Synthesis
, vol.147
-
-
Ikoma, Y.1
Taya, F.2
Ozaki, E.-I.3
Higuchi, S.4
Naoi, Y.5
Fuji-i, K.6
-
79
-
-
0025892734
-
-
For further examples of cross-coupling reactions of aryl halides with only aromatic Grignard reagents catalyzed by nonligated nickel, see: (a) Ikoma, Y.; Taya, F.; Ozaki, E.-i.; Higuchi, S.; Naoi, Y.; Fuji-i, K. Synthesis 1990, 147. (b) Ikoma, Y.; Ando, K.; Naoi, Y.; Akiyama, T.; Sugimori, A. Synth. Commun. 1991, 21, 481.
-
(1991)
Synth. Commun.
, vol.21
, pp. 481
-
-
Ikoma, Y.1
Ando, K.2
Naoi, Y.3
Akiyama, T.4
Sugimori, A.5
-
80
-
-
0037165715
-
-
2 was also used recently for cross-couplings of alkyl halides with alkyl Grignard reagents. Similar to our results, ligandless reactions did not provide the desired products, addition of 1,3-butadiene derivatives as ligands was required. Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 4222
-
-
Terao, J.1
Watanabe, H.2
Ikumi, A.3
Kuniyasu, H.4
Kambe, N.5
-
82
-
-
0000982708
-
-
(a) Böhm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Herrmann, W. A. Angew. Chem. 2000, 112, 1672; Angew. Chem., Int. Ed. 2000, 39, 1602.
-
(2000)
Angew. Chem.
, vol.112
, pp. 1672
-
-
Böhm, V.P.W.1
Weskamp, T.2
Gstöttmayr, C.W.K.3
Herrmann, W.A.4
-
83
-
-
0037484660
-
-
(a) Böhm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Herrmann, W. A. Angew. Chem. 2000, 112, 1672; Angew. Chem., Int. Ed. 2000, 39, 1602.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 1602
-
-
-
85
-
-
0001113068
-
-
Fürstner, A.; Leitner, A. Angew. Chem. 2002, 114, 632; Angew. Chem., Int. Ed. 2002, 41, 609.
-
(2002)
Angew. Chem.
, vol.114
, pp. 632
-
-
Fürstner, A.1
Leitner, A.2
-
86
-
-
0037083916
-
-
Fürstner, A.; Leitner, A. Angew. Chem. 2002, 114, 632; Angew. Chem., Int. Ed. 2002, 41, 609.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 609
-
-
|