-
1
-
-
0345329013
-
-
For reviews, see: (a) Lindley, J. Tetrahedron 1984, 40, 1433.
-
(1984)
Tetrahedron
, vol.40
, pp. 1433
-
-
Lindley, J.1
-
2
-
-
0345708168
-
-
(b) 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
-
7
-
-
0034794463
-
-
(a) 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
-
8
-
-
0035891639
-
-
(b) Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
-
(2001)
Org. Lett.
, vol.3
, pp. 3803
-
-
Wolter, M.1
Klapars, A.2
Buchwald, S.L.3
-
9
-
-
0037178121
-
-
(c) 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
-
10
-
-
37049061223
-
-
For examples where increasing the [ligand] inhibits copper-promoted reactions, see: (a) Bacon, R. G. R.; Hill, H. A. O. J. Chem. Soc. 1964, 1097.
-
(1964)
J. Chem. Soc.
, pp. 1097
-
-
Bacon, R.G.R.1
Hill, H.A.O.2
-
11
-
-
12344254000
-
-
(b) Rusonik, I.; Cohen, H.; Meyerstein, D. J. Chem. Soc., Dalton Trans. 2003, 2024. For examples of ligand-accelerated copper-catalyzed reactions, see:
-
(2003)
J. Chem. Soc., Dalton Trans.
, pp. 2024
-
-
Rusonik, I.1
Cohen, H.2
Meyerstein, D.3
-
13
-
-
0033515805
-
-
(d) 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
-
14
-
-
0034738131
-
-
(e) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 5043
-
-
Fagan, P.J.1
Hauptman, E.2
Shapiro, R.3
Casalnuovo, A.4
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15
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16244422422
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note
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One explanation for the activity of catalysts based on 1,2-diamines is that they increase the oxidation potential of copper(I), thus facilitating the activation of the aryl halide; see ref 4b.
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16
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0006019623
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(a) 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
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18
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0041701459
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(c) Blue, E. D.; Davis, A.; Conner, D.; Gunnoe, T. B.; Boyle, P. D.; White, P. S. J. Am. Chem. Soc. 2003, 125, 9435.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 9435
-
-
Blue, E.D.1
Davis, A.2
Conner, D.3
Gunnoe, T.B.4
Boyle, P.D.5
White, P.S.6
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19
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0037184431
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(a) Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14104.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 14104
-
-
Singh, U.K.1
Strieter, E.R.2
Blackmond, D.G.3
Buchwald, S.L.4
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20
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1042265088
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(b) Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 1360
-
-
Nielsen, L.P.C.1
Stevenson, C.P.2
Blackmond, D.G.3
Jacobsen, E.N.4
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21
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16244384277
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note
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4 may limit the reaction rate due to mass transfer effects. However, using different stirring rates resulted in identical reaction rate profiles, thus ruling out the possibility of a mass transfer limited process.
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23
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16244409349
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note
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See Supporting Information.
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24
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16244405967
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note
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T, and [Amide] simplify eq 2 to the form: rate = a[3]/(1 + b[3]), where a and b are adjustable parameters.
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25
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16244377820
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note
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Reaction rate is independent of [base] at both low and high [3]. This is presumably due to saturation of the base in a nonpolar solvent, and thus, the [base] is treated as a constant. See Supporting Information for more details.
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26
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0000510143
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For the synthesis of copper(I) amides, see: (a) Tsuda, T.; Watanabe, K.; Miyata, K.; Yamamoto, H.; Saegusa, T. Inorg. Chem. 1981, 20, 2728.
-
(1981)
Inorg. Chem.
, vol.20
, pp. 2728
-
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Tsuda, T.1
Watanabe, K.2
Miyata, K.3
Yamamoto, H.4
Saegusa, T.5
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28
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(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
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-
Gamboratta, S.1
Bracci, M.2
Floriani, C.3
Chiesi-Villa, A.4
Guastini, C.5
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29
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16244391200
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note
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Arylation of 5 in the absence of 3 did not proceed at temperatures between 0 °C and 90 °C.
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