-
5
-
-
0345329013
-
-
For an older review highlighting the application of the Ullmann/Goldberg reaction in synthesis, see: Lindley, J. Tetrahedron 1984, 40, 1433.
-
For an older review highlighting the application of the Ullmann/Goldberg reaction in synthesis, see: Lindley, J. Tetrahedron 1984, 40, 1433.
-
-
-
-
6
-
-
24144441333
-
Palladium-Catalyzed Aromatic Carbon- Nitrogen Bond Formation
-
For reviews on palladium-catalyzed C-N bond formation, see: a, 2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim
-
For reviews on palladium-catalyzed C-N bond formation, see: (a) Jiang, L.; Buchwald, S. L. Palladium-Catalyzed Aromatic Carbon- Nitrogen Bond Formation. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; p 699.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
, pp. 699
-
-
Jiang, L.1
Buchwald, S.L.2
-
9
-
-
14844330054
-
-
(a) Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 1371
-
-
Shen, Q.1
Shekhar, S.2
Stambuli, J.P.3
Hartwig, J.F.4
-
10
-
-
0038579438
-
-
(b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 6653
-
-
Huang, X.1
Anderson, K.W.2
Zim, D.3
Jiang, L.4
Klapars, A.5
Buchwald, S.L.6
-
11
-
-
0011411784
-
-
(c) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885.
-
(2002)
Org. Lett
, vol.4
, pp. 2885
-
-
Harris, M.C.1
Huang, X.2
Buchwald, S.L.3
-
12
-
-
0035938374
-
-
(d) Link, J. T.; Sorensen, B.; Liu, G.; Pei, Z.; Reilly, E. B.; Leitza, S.; Okasinski, G. Bioorg. Med. Chem. Lett. 2001, 11, 973.
-
(2001)
Bioorg. Med. Chem. Lett
, vol.11
, pp. 973
-
-
Link, J.T.1
Sorensen, B.2
Liu, G.3
Pei, Z.4
Reilly, E.B.5
Leitza, S.6
Okasinski, G.7
-
13
-
-
0034696969
-
-
(e) Prashad, M.; Hu, B.; Lu, Y.; Draper, R.; Har, D.; Repic, O.; Blacklock, T. J. J. Org. Chem. 2000, 65, 2612.
-
(2000)
J. Org. Chem
, vol.65
, pp. 2612
-
-
Prashad, M.1
Hu, B.2
Lu, Y.3
Draper, R.4
Har, D.5
Repic, O.6
Blacklock, T.J.7
-
18
-
-
0035833683
-
-
(b) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539.
-
(2001)
Org. Lett
, vol.3
, pp. 2539
-
-
Cacchi, S.1
Fabrizi, G.2
Goggiamani, A.3
Zappia, G.4
-
19
-
-
0035948232
-
-
(c) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron. Lett. 2001, 42, 4381.
-
(2001)
Tetrahedron. Lett
, vol.42
, pp. 4381
-
-
Artamkina, G.A.1
Sergeev, A.G.2
Beletskaya, I.P.3
-
22
-
-
0033515805
-
-
Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 2657
-
-
Kiyomori, A.1
Marcoux, J.-F.2
Buchwald, S.L.3
-
24
-
-
0001572402
-
-
Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
-
(2001)
Org. Lett
, vol.3
, pp. 4315
-
-
Gujadhur, R.K.1
Bates, C.G.2
Venkataraman, D.3
-
25
-
-
0037149057
-
-
Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Jett. 2002, 4, 581.
-
(2002)
Org. Jett
, vol.4
, pp. 581
-
-
Kwong, F.Y.1
Klapars, A.2
Buchwald, S.L.3
-
26
-
-
0141854366
-
-
Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
-
(2003)
Org. Lett
, vol.5
, pp. 2453
-
-
Ma, D.1
Cai, Q.2
Zhang, H.3
-
28
-
-
4143104684
-
-
(a) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J Org. Chem. 2004, 69, 5578.
-
(2004)
J Org. Chem
, vol.69
, pp. 5578
-
-
Antilla, J.C.1
Baskin, J.M.2
Barder, T.E.3
Buchwald, S.L.4
-
29
-
-
0037433554
-
-
(b) Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 2890
-
-
Zanon, J.1
Klapars, A.2
Buchwald, S.L.3
-
30
-
-
0142106421
-
-
(c) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667.
-
(2003)
Org. Lett
, vol.5
, pp. 3667
-
-
Jiang, L.1
Job, G.E.2
Klapars, A.3
Buchwald, S.L.4
-
32
-
-
0037009958
-
-
(e) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 11684
-
-
Antilla, J.C.1
Klapars, A.2
Buchwald, S.L.3
-
33
-
-
0037178121
-
-
(f) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 7421
-
-
Klapars, A.1
Huang, X.2
Buchwald, S.L.3
-
34
-
-
0034794463
-
-
(g) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 7727
-
-
Klapars, A.1
Antilla, J.C.2
Huang, X.3
Buchwald, S.L.4
-
35
-
-
9644277114
-
-
For a critical review concerning copper-catalyzed cross coupling reactions, see
-
For a critical review concerning copper-catalyzed cross coupling reactions, see: Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
-
(2004)
Coord. Chem. Rev
, vol.248
, pp. 2337
-
-
Beletskaya, I.P.1
Cheprakov, A.V.2
-
36
-
-
0345708168
-
-
(a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
-
(2003)
Angew. Chem., Int. Ed
, vol.42
, pp. 5400
-
-
Ley, S.V.1
Thomas, A.W.2
-
37
-
-
0346749657
-
-
(b) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 15, 2428.
-
(2003)
Synlett
, vol.15
, pp. 2428
-
-
Kunz, K.1
Scholz, U.2
Ganzer, D.3
-
42
-
-
0001531512
-
-
(a) Aalten, H. L.; van Koten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A. Tetrahedron 1989, 45, 5565.
-
(1989)
Tetrahedron
, vol.45
, pp. 5565
-
-
Aalten, H.L.1
van Koten, G.2
Grove, D.M.3
Kuilman, T.4
Piekstra, O.G.5
Hulshof, L.A.6
Sheldon, R.A.7
-
43
-
-
33947478767
-
-
(b) Resnik, R.; Cohen, T.; Fernando, Q. J. Am. Chem. Soc. 1961, 83, 3344.
-
(1961)
J. Am. Chem. Soc
, vol.83
, pp. 3344
-
-
Resnik, R.1
Cohen, T.2
Fernando, Q.3
-
45
-
-
0001626821
-
-
Whitesides, G. M.; Sadowski, J. S.; Lilburn, J. J. Am. Chem. Soc. 1974, 96, 2829.
-
(1974)
J. Am. Chem. Soc
, vol.96
, pp. 2829
-
-
Whitesides, G.M.1
Sadowski, J.S.2
Lilburn, J.3
-
46
-
-
0006019623
-
-
Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1980, 53, 1299.
-
(1980)
Bull. Chem. Soc. Jpn
, vol.53
, pp. 1299
-
-
Yamamoto, T.1
Ehara, Y.2
Kubota, M.3
Yamamoto, A.4
-
47
-
-
16244411305
-
-
(a) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 4120
-
-
Strieter, E.R.1
Blackmond, D.G.2
Buchwald, S.L.3
-
48
-
-
67849132776
-
-
Ph.D. Thesis, Massachusetts Institute of Technology
-
(b) Strieter, E. R., Ph.D. Thesis, Massachusetts Institute of Technology, 2005.
-
(2005)
-
-
Strieter, E.R.1
-
49
-
-
48249117090
-
-
Tye, J. W.; Weng, Z.; Johns, A. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 9971.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 9971
-
-
Tye, J.W.1
Weng, Z.2
Johns, A.M.3
Incarvito, C.D.4
Hartwig, J.F.5
-
50
-
-
84869555771
-
-
This time lapse manifests itself as a plateau in the concentration vs time profiles; thus, in some of the figures, e.g, Figures 4-6, the data at the beginning of the reaction is not shown. Moreover, in some instances, an induction period lasting until approximately 15% conversion is observed. The length of the induction period, i.e, whether it lasts until 5% conversion or until 15% conversion, was not always reproducible. The method in which the inorganic base was dried and stored clearly had an effect on this induction period, and reproducible results for the remainder of the reaction, once the induction period subsided, were only obtained with K3PO4 available from Fluka catalog number 04347, Riedel-de Haën product; free-flowing, fine granules of uniform size, K3PO4 was dried under high vacuum at 150 °C for 3 days and stored in a nitrogen-filled glovebox. Based on these observations, we suspect that the induction period is not m
-
4 was dried under high vacuum at 150 °C for 3 days and stored in a nitrogen-filled glovebox. Based on these observations, we suspect that the induction period is not mechanistically relevant.
-
-
-
-
51
-
-
67849103161
-
-
Due to the limited solubility of K3PO4 in toluene, it is difficult to estimate the concentrations. Thus, the values for [K 3PO4]0 are reported in millimoles of K 3PO4 used in the reaction
-
4 used in the reaction.
-
-
-
-
52
-
-
84869579450
-
-
2 are adjustable parameters.
-
2 are adjustable parameters.
-
-
-
-
53
-
-
0346242790
-
-
For previous characterization of related structures, see: a
-
For previous characterization of related structures, see: (a) Raubenheimer, H. G.; Cronje, S.; Kruger, G. J.; Olivier, P. J. Polyhedron 1995, 14, 2389.
-
(1995)
Polyhedron
, vol.14
, pp. 2389
-
-
Raubenheimer, H.G.1
Cronje, S.2
Kruger, G.J.3
Olivier, P.J.4
-
54
-
-
24544438306
-
-
(b) Davies, G.; El-Kady, N.; Onan, K. D.; Shomaly, W.; El-Sayed, M. A.; El-Toukhy, A. Inorg. Chim. Acta 1988, 149, 21.
-
(1988)
Inorg. Chim. Acta
, vol.149
, pp. 21
-
-
Davies, G.1
El-Kady, N.2
Onan, K.D.3
Shomaly, W.4
El-Sayed, M.A.5
El-Toukhy, A.6
-
55
-
-
0040191445
-
-
(c) Davies, G.; El-Kady, N.; El-Sayed, M. A.; El-Toukhy, A.; Schure, M. R. Inorg. Chim. Acta 1988, 149, 31.
-
(1988)
Inorg. Chim. Acta
, vol.149
, pp. 31
-
-
Davies, G.1
El-Kady, N.2
El-Sayed, M.A.3
El-Toukhy, A.4
Schure, M.R.5
-
56
-
-
37049110223
-
-
(d) Healy, P. C.; Pakawatchai, C.; White, A. H. J. Chem. Soc., Dalton Trans. 1985, 2531.
-
(1985)
J. Chem. Soc., Dalton Trans
, pp. 2531
-
-
Healy, P.C.1
Pakawatchai, C.2
White, A.H.3
-
58
-
-
67849123748
-
-
Enantiomerically pure (R,R)-3 was used to obtain X-ray quality crystals.
-
Enantiomerically pure (R,R)-3 was used to obtain X-ray quality crystals.
-
-
-
-
59
-
-
84869579448
-
-
total. These results suggest that the dimeric complex is not a kinetically relevant species.
-
total. These results suggest that the dimeric complex is not a kinetically relevant species.
-
-
-
-
60
-
-
67849086315
-
-
(a) Tsuda, T.; Yazawa, T.; Watanabe, K.; Fujii, T.; Saegusa, T. J. Org. Chem. 1981, 46, 292.
-
(1981)
J. Org. Chem
, vol.46
, pp. 292
-
-
Tsuda, T.1
Yazawa, T.2
Watanabe, K.3
Fujii, T.4
Saegusa, T.5
-
61
-
-
37049100164
-
-
(b) Gambarotta, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Chem Soc., Commun., 1983, 1156.
-
(1983)
J. Chem Soc., Commun
, pp. 1156
-
-
Gambarotta, S.1
Floriani, C.2
Chiesi-Villa, A.3
Guastini, C.4
-
62
-
-
0000727781
-
-
(c) Meyer, E. M.; Gambarotta, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Organometallics 1989, 8, 1067.
-
(1989)
Organometallics
, vol.8
, pp. 1067
-
-
Meyer, E.M.1
Gambarotta, S.2
Floriani, C.3
Chiesi-Villa, A.4
Guastini, C.5
-
64
-
-
4243785018
-
-
Eriksson, H.; Hå&kansson, M. Organometallics 1997, 16, 4243.
-
(e) Eriksson, H.; Hå&kansson, M. Organometallics 1997, 16, 4243.
-
-
-
-
65
-
-
0000510143
-
-
For the synthesis of copper(I)-amides, see: (a) Tsuda, T.; Watanabe, K.; Miyata, K.; Yamamoto, H.; Saegusa, T. Inorg. Chem. 1981, 20, 2728.
-
For the synthesis of copper(I)-amides, see: (a) Tsuda, T.; Watanabe, K.; Miyata, K.; Yamamoto, H.; Saegusa, T. Inorg. Chem. 1981, 20, 2728.
-
-
-
-
67
-
-
37049067364
-
-
(c) Gamboratta, S.; Bracci, M.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Chem. Soc., Dalton Trans. 1987, 1883.
-
(1987)
J. Chem. Soc., Dalton Trans
, pp. 1883
-
-
Gamboratta, S.1
Bracci, M.2
Floriani, C.3
Chiesi-Villa, A.4
Guastini, C.5
-
68
-
-
67849107861
-
-
A similar procedure was used to characterize Cu(I) alkoxides; see ref 20
-
(32) A similar procedure was used to characterize Cu(I) alkoxides; see ref 20.
-
-
-
-
69
-
-
0000709468
-
-
(a) Lopes, C.; Håkansson, M.; Jagner, S. Inorg. Chim. Acta 1997, 254, 361.
-
(1997)
Inorg. Chim. Acta
, vol.254
, pp. 361
-
-
Lopes, C.1
Håkansson, M.2
Jagner, S.3
-
70
-
-
0034733407
-
-
(b) Håkansson, M.; Lopes, C.; Jagner, S. Inorg. Chim. Acta 2000, 304, 178.
-
(2000)
Inorg. Chim. Acta
, vol.304
, pp. 178
-
-
Håkansson, M.1
Lopes, C.2
Jagner, S.3
-
71
-
-
0037156310
-
-
(c) Gustafsson, B.; Håkansson, M.; Westman, G.; Jagner, S. J. Organomet. Chem. 2002, 649, 204.
-
(2002)
J. Organomet. Chem
, vol.649
, pp. 204
-
-
Gustafsson, B.1
Håkansson, M.2
Westman, G.3
Jagner, S.4
-
72
-
-
1042288491
-
-
(34) Hibble, S. J.; Eversfield, S. G.; Cowley, A. R.; Chippindale, A. M. Angew. Chem., Int. Ed. 2004, 43, 628.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 628
-
-
Hibble, S.J.1
Eversfield, S.G.2
Cowley, A.R.3
Chippindale, A.M.4
-
74
-
-
0002522541
-
Experimental Organometallic Chemistry: A Practice in Synthesis and Characterization
-
Wayada, A. L, Darensbourg, M. Y, Eds, American Chemical Society, Washington, DC, Chapter 4, pp
-
(b) Burger, B. J.; Bercaw, J. E. In Experimental Organometallic Chemistry: A Practice in Synthesis and Characterization, Wayada, A. L., Darensbourg, M. Y., Eds.; ACS Symposium Series 357: American Chemical Society, Washington, DC, 1987: Chapter 4, pp 94-96.
-
(1987)
ACS Symposium Series
, vol.357
, pp. 94-96
-
-
Burger, B.J.1
Bercaw, J.E.2
-
76
-
-
84869555764
-
-
Arylation of Cu(I) amidate in the absence of 3 did not proceed at temperatures between 0 and 90 °C.
-
(36) Arylation of Cu(I) amidate in the absence of 3 did not proceed at temperatures between 0 and 90 °C.
-
-
-
-
77
-
-
84869575784
-
-
3-ligated Cu(I) amidates also undergo N-arylations; however, these reactions were not kinetically characterized either stoichiometrically or in the context of a catalytic reaction.
-
3-ligated Cu(I) amidates also undergo N-arylations; however, these reactions were not kinetically characterized either stoichiometrically or in the context of a catalytic reaction.
-
-
-
-
82
-
-
0001213888
-
-
a
-
(40) (a) Whitesides, G. M.; Fischer, W. F.; San Filippo, J.; Bashe, R. W.; House, H. O. J. Am. Chem. Soc. 1969, 91, 4871.
-
(1969)
J. Am. Chem. Soc
, vol.91
, pp. 4871
-
-
Whitesides, G.M.1
Fischer, W.F.2
San Filippo, J.3
Bashe, R.W.4
House, H.O.5
-
85
-
-
0002845031
-
-
(a) Cohen, T.; Wood, J.; Dietz, A. G. Tetrahedron Lett. 1974, 40, 3555.
-
(1974)
Tetrahedron Lett
, vol.40
, pp. 3555
-
-
Cohen, T.1
Wood, J.2
Dietz, A.G.3
-
86
-
-
0001358527
-
-
(b) Cohen, T.; Lewarchik, R. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753.
-
(1974)
J. Am. Chem. Soc
, vol.96
, pp. 7753
-
-
Cohen, T.1
Lewarchik, R.J.2
Tarino, J.Z.3
-
88
-
-
12944316680
-
-
(43) Arai, S.; Hida, M.; Yamagishi, T. Bull. Chem. Soc. Jpn. 1978, 51, 277.
-
(1978)
Bull. Chem. Soc. Jpn
, vol.51
, pp. 277
-
-
Arai, S.1
Hida, M.2
Yamagishi, T.3
-
89
-
-
37049094651
-
-
Bethell, D.; Jenkins, I. L.; Quan, P. M. J. Chem. Soc., Perkin Trans. 2 1985, 1789.
-
(1985)
J. Chem. Soc., Perkin Trans. 2
, pp. 1789
-
-
Bethell, D.1
Jenkins, I.L.2
Quan, P.M.3
-
92
-
-
33749129825
-
-
For studies demonstrating the relative affinities of aromatic acids to Cu(I), see: (a) Saphier, M.; Burg, A.; Sheps, S.; Cohen, H.; Meyerstein, D. J. Chem. Soc., Dalton Trans. 1999, 1845.
-
For studies demonstrating the relative affinities of aromatic acids to Cu(I), see: (a) Saphier, M.; Burg, A.; Sheps, S.; Cohen, H.; Meyerstein, D. J. Chem. Soc., Dalton Trans. 1999, 1845.
-
-
-
-
93
-
-
34548591384
-
-
Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Organometallics 2007, 26, 4546.
-
(2007)
Organometallics
, vol.26
, pp. 4546
-
-
Zhang, S.-L.1
Liu, L.2
Fu, Y.3
Guo, Q.-X.4
-
94
-
-
67849132021
-
-
While this manuscript was being prepared, ref 23 was published, which provides experimental evidence that an intermediate such as C in Scheme 4 is unreactive toward aryl iodides and aryl bromides
-
While this manuscript was being prepared, ref 23 was published, which provides experimental evidence that an intermediate such as C in Scheme 4 is unreactive toward aryl iodides and aryl bromides.
-
-
-
-
95
-
-
67849113603
-
-
Nonlinear least-squares fits to eq 9 were obtained by using the Solver function within Microsoft Excel.
-
Nonlinear least-squares fits to eq 9 were obtained by using the Solver function within Microsoft Excel.
-
-
-
|