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7
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0037112673
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For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: (g) A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4211
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Fu, G.C.2
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T.H.M. Jonckers, B.U.W. Maes, G.L.F. Lemière, G. Rombouts, L. Pieters, A. Haemers, and R.A. Dommisse Synlett 2003 615 618
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Jonckers, T.H.M.1
Maes, B.U.W.2
Lemière, G.L.F.3
Rombouts, G.4
Pieters, L.5
Haemers, A.6
Dommisse, R.A.7
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15
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0032541736
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G.J. Tanoury, C.H. Senanayaka, R. Hett, A.M. Kuhn, D.W. Kessler, and S.A. Wald Tetrahedron Lett. 39 1998 6845 6848
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Tanoury, G.J.1
Senanayaka, C.H.2
Hett, R.3
Kuhn, A.M.4
Kessler, D.W.5
Wald, S.A.6
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0242710844
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G.J. Tanoury, R. Hett, H.S. Wilkinson, S.A. Wald, and C.H. Senanayake Tetrahedron: Assymmetry 14 2003 3487 3493
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Tetrahedron: Assymmetry
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Tanoury, G.J.1
Hett, R.2
Wilkinson, H.S.3
Wald, S.A.4
Senanayake, C.H.5
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17
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0030763062
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Y. Hong, G.J. Tanoury, H.S. Wilkinson, R.P. Bakale, S.A. Wald, and C.H. Senanayaka Tetrahedron Lett. 38 1997 5607 5610
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Hong, Y.1
Tanoury, G.J.2
Wilkinson, H.S.3
Bakale, R.P.4
Wald, S.A.5
Senanayaka, C.H.6
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18
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0037122141
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Recently, an interesting article appeared dealing with fast (15 min) room temperature Pd-catalyzed aminations of activated and unactivated aryl chlorides using alkyl di-t-butylphosphane ligated palladium(I) dimers. Unfortunately, the scope of this exceptionally fast room-temperature amination chemistry is narrow: (a) J.P. Stambuli, R. Kuwano, and J.F. Hartwig Angew. Chem., Int. Ed. 41 2002 4746 4748
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(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 4746-4748
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Stambuli, J.P.1
Kuwano, R.2
Hartwig, J.F.3
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19
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0034712156
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Although, also other catalysts have been used to perform Buchwald-Hartwig aminations at room temperature the scope is generally broader at higher temperature. Moreover, the reaction times for couplings at room temperature are in the order of hours to one day: (b) J.P. Wolfe, H. Tomori, J.P. Sadighi, J. Yin, and S.L.J. Buchwald J. Org. Chem. 65 2000 1158 1174
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(2000)
J. Org. Chem.
, vol.65
, pp. 1158-1174
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Wolfe, J.P.1
Tomori, H.2
Sadighi, J.P.3
Yin, J.4
Buchwald, S.L.J.5
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20
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0034682151
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S.R. Stauffer, S. Lee, J.P. Stambuli, S.I. Hauck, and J.F. Hartwig Org. Lett. 2 2000 1423 1426
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(2000)
Org. Lett.
, vol.2
, pp. 1423-1426
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Stauffer, S.R.1
Lee, S.2
Stambuli, J.P.3
Hauck, S.I.4
Hartwig, J.F.5
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30
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0347717654
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Between the publication of our short communication (see Ref. 9) and this manuscript Caddick and co-workers reported microwave-assisted amination of aryl chlorides using palladium-N-heterocyclic carbene complexes as catalyst: A.J. McCarroll, D.A. Sandham, L.R. Titcomb, A.K. Lewis, F.G.N. Cloke, B.P. Davies, A. Perez de Santana, W. Hiller, and S. Caddick Mol. Divers. 7 2003 115 123
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(2003)
Mol. Divers.
, vol.7
, pp. 115-123
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McCarroll, A.J.1
Sandham, D.A.2
Titcomb, L.R.3
Lewis, A.K.4
Cloke, F.G.N.5
Davies, B.P.6
Perez De Santana, A.7
Hiller, W.8
Caddick, S.9
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31
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0033549829
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For the amination of aryl chlorides under classical heating using a palladium catalyst based on an electron rich monophosphanylbiaryl ligand see: (a) J.P. Wolfe, and S.L. Buchwald Angew. Chem., Int. Ed. 38 1999 2413 2416
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(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2413-2416
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Wolfe, J.P.1
Buchwald, S.L.2
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32
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8644257184
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See Ref. 8b.
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(b) See Ref. 8b.
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35
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8644276762
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note
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According to the 'Strem Chemicals' catalogue (2001-2003) 2 g DCPB costs 165 Euro, 2 g DTPB costs 165 Euro and 2 g DCPAB costs 269 Euro.
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37
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57249108155
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For the intermolecular microwave-assisted palladium-catalyzed amination of aryl bromides see: (a) A. Sharifi, R. Hosseinzadeh, and M. Mirzaei Monatsh. Chem. 133 2002 329 332
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(2002)
Monatsh. Chem.
, vol.133
, pp. 329-332
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Sharifi, A.1
Hosseinzadeh, R.2
Mirzaei, M.3
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42
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0043009828
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For the intramolecular microwave-assisted palladium-catalyzed amination of aryl bromides see: C.T. Brain, and J.T. Steer J. Org. Chem. 68 2003 6814 6816
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(2003)
J. Org. Chem.
, vol.68
, pp. 6814-6816
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Brain, C.T.1
Steer, J.T.2
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44
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0033597748
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J.F. Hartwig, M. Kawatsura, S.I. Hauck, K.H. Shaughnessy, and L.M. Alcazar-Roman J. Org. Chem. 64 1999 5575 5580
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(1999)
J. Org. Chem.
, vol.64
, pp. 5575-5580
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Hartwig, J.F.1
Kawatsura, M.2
Hauck, S.I.3
Shaughnessy, K.H.4
Alcazar-Roman, L.M.5
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45
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84862464139
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2/DTPB at least for 16 h before using it: see Ref. 12d.
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2/DTPB at least for 16 h before using it: see Ref. 12d.
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48
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8644224538
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note
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In control microwave experiments the amination reactions studied were also executed without the use of Pd-catalyst under otherwise identical reaction conditions. The obtained results clearly indicate that these reactions require the use of transition metal catalyst.
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49
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8644223670
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note
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It was not attempted to check whether the studied microwave-assisted aminations were not already finished before 10 minutes. Theoretically, the possibility of a specific microwave effect can therefore not be ruled out. Nevertheless, if there is such a microwave effect, it is surely very small.
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