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(a) Hegedus L. S. In Organometallics in Synthesis; Schlösser, M., Ed.; Wiley: New York, 1994; Chapter 5, pp 385-459.
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Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, Chapter 8.2
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(e) Harrington P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 8.2, pp 798-903.
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9
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0000492007
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To the best of our knowledge, we could find only two nonrationalized precedents of Pd(0)-catalyzed allylic alkylations using allylic acetates in the absence of bases, (a)
-
To the best of our knowledge, we could find only two nonrationalized precedents of Pd(0)-catalyzed allylic alkylations using allylic acetates in the absence of bases, (a) Moreno-Manas, M.; Prat, M.; Ribas, J.; Virgili, A. Tetrahedron Lett. 1988,29, 581.
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(b) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970,11, 3821.
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Atkins, K.E.1
Walker, W.E.2
Manyik, R.M.3
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11
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0344887064
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Ethyl nitroacetate
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Sources of the pK, values reported in Table 1. (Phenylsulfonyl)nitromethane, barbituric acid, malononitrile, Meldrum's acid, bis(phenylsulfonyDmethane, ethyl acetoacetate, diethyl malonate: (a) Bordwell, F. G. Ace. Chem. Res. 1988, 21, 456. Ethyl nitroacetate:
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Bordwell, F.G.1
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(b) Hashida, Y.; Kobayashi, M.; Matsui, K. Bull. Chem. Soc. Jpn. 1971,44,2506.
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Hashida, Y.1
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Matsui, K.3
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13
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3543021019
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The pK, values of methyl phenylsulfonyl acetate and of ethyl nitroacetate in DMSO have been estimated.
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Pearson, R. G.; Dillon, R. L. J. Am. Chem. Soc. 1953, 75, 2439. The pK, values of methyl phenylsulfonyl acetate and of ethyl nitroacetate in DMSO have been estimated.
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Pearson, R.G.1
Dillon, R.L.2
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Tsuji, J.; Okumoto, H.; Kobayashi, Y.; Takahashi, T. Tetrahedron Lett. 1981,22, 1357.
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Tsuji, J.1
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Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981,22,2575.
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Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451.
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Wagaw, S.1
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Buchwald, S.L.3
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18
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0000016787
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In a recent example of palladium-catalyzed C-Mitsunobu condensation a similar palladium complex has been postulated
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In a recent example of palladium-catalyzed C-Mitsunobu condensation a similar palladium complex has been postulated: Shing, T. K M.; Li, L.-H.; Narkunan K. J. Org. Chem. 1997, 62, 1617.
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Shing, T.K.M.1
Li, L.-H.2
Narkunan, K.3
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19
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0004143671
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Such a coordination is also expected to synergistically enhance the acidity of the Pd(II)-coordinated active méthylènes, (a) VCH: Weinheim
-
Such a coordination is also expected to synergistically enhance the acidity of the Pd(II)-coordinated active méthylènes, (a) Constable, E. C. Metals'and Ligand Reactivity; VCH: Weinheim, 1995.
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Metals'and Ligand Reactivity
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Constable, E.C.1
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15844412400
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(b) Murahashi, S.I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, I.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117,12436.
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Naota, T.2
Taki, H.3
Mizuno, M.4
Takaya, H.5
Komiya, S.6
Mizuho, I.7
Oyasato, N.8
Hiraoka, M.9
Hirano, M.10
Fukuoka, A.11
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21
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33847510992
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At present, an alternative path involving the transient formation of a σ-allyl Pd complex maintaining two trans-disposed phophines cannot be ruled out.
-
At present, an alternative path involving the transient formation of a σ-allyl Pd complex maintaining two trans-disposed phophines cannot be ruled out.
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22
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37049131592
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Takahashi, Y.; Sakai, S.; Ishii, Y. J. Chem. Soc., Chem. Commun. 1967, 1092.
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Takahashi, Y.1
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23
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33847511197
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The pK. values of HC1 and AcOH in DMSO are 1.8 and 12.3, respectively. See ref lOa.
-
The pK. values of HC1 and AcOH in DMSO are 1.8 and 12.3, respectively. See ref lOa.
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-
-
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24
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0023850740
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For reported examples of Pd-catalyzed allylic alkylations of active méthylènes in the presence of bases, or using already deprotonated nucleophiles, see, for example: (a)
-
For reported examples of Pd-catalyzed allylic alkylations of active méthylènes in the presence of bases, or using already deprotonated nucleophiles, see, for example: (a) Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988, 770,621.
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Trost, B.M.1
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0000776017
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Wade P. A.; Hinney, H. R.; Amin, N. V.; Vail, P. D.; Morrow, S. D.; Hardinger, S. A.; Saft, M. S. J. Org. Chem. 1981, 46, 765.
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Vail, P.D.4
Morrow, S.D.5
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0000630216
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Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379.
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0342683567
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(e) Prat, M.; Moreno-Manas, M.; Ribas, J. Tetrahedron 1988,44,7205.
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Prat, M.1
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29
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0000903824
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A related Pd(0)-catalyzed condensation between active méthylènes ' and aliènes under neutral conditions has been recently reported. In that case, the mechanism has been rationalized on the basis of the initial oxidative addition of Pd(0) into the C-H bond of the active méthylène followed by carbopalladation.
-
A related Pd(0)-catalyzed condensation between active méthylènes ' and aliènes under neutral conditions has been recently reported. (Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 776, 6019). In that case, the mechanism has been rationalized on the basis of the initial oxidative addition of Pd(0) into the C-H bond of the active méthylène followed by carbopalladation.
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J. Am. Chem. Soc.
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Yamamoto, Y.1
Al-Masum, M.2
Asao, N.3
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