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Discovery and early references: a) J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, Angew. Chem. 1959, 71, 176-182;
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b) J. Smidt, W. Hafner, J. Jira, R. Sieber, J. Sedlmeier, J. Sable, Angew. Chem. Int. Ed. Engl. 1962, 1, 80-88;
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Smidt, J.1
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Sieber, R.4
Sedlmeier, J.5
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84981759211
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c) W. Hafner, R. Jira, J. Sedlmeier, J. Smidl, Chem. Ber. 1962, 95, 1575-1581.
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5
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0242617658
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(Ed.: E.-I. Negishi), Wiley Interscience, New York
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e) P. M. Henry, in Handbook of Organopalladium Chemistry for Organic Synthesis, vol. 2 (Ed.: E.-I. Negishi), Wiley Interscience, New York, 2002, pp. 2119-2140.
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Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2
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Henry, P.M.1
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6
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0003690482
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D. Riedel Pub. Co., Dordrecht (Netherlands)
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For an overview of the lead mechanistic studies on the Wacker reaction to 1980, see: P. M. Henry, Palladium Catalyzed Oxidation of Hydrocarbons, D. Riedel Pub. Co., Dordrecht (Netherlands), 1980.
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Palladium Catalyzed Oxidation of Hydrocarbons
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Henry, P.M.1
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7
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0242617658
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(Ed.: E.-I. Negishi), Wiley Interscience, New York
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For more recent advances, see: P. M. Henry, in Handbook, of Organopalladium Chemistry for Organic Synthesis, vol. 2 (Ed.: E.-I. Negishi), Wiley Interscience, New York, 2002, pp. 2119-2140.
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Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2
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Henry, P.M.1
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8
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85083243520
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For reviews see: a) J. Tsuji. Synthesis 1984, 369-384;
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Synthesis
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Tsuji, J.1
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11
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0001046067
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J. Tsuji, I. Shimizu, K. Yamamoto, Tetrahedron Lett. 1976, 17, 2975-2976.
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Tetrahedron Lett.
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Tsuji, J.1
Shimizu, I.2
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12
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0000384387
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See for example: a) A. K. Bose, L. Krishnan, D. R. Wagle, M. S. Manhas. Tetrahedron Lett. 1986, 27, 5955-5958;
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Tetrahedron Lett.
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Bose, A.K.1
Krishnan, L.2
Wagle, D.R.3
Manhas, M.S.4
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13
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0030961403
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b) H. Pellissier, P.- Y. Michellys, M. Santelli, Tetrahedron Lett. 1997, 38, 7577-7586;
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Tetrahedron Lett.
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Pellissier, H.1
Michellys, P.Y.2
Santelli, M.3
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14
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0000508605
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c) S.-K. Kang, K.-Y. Jung, J.-U. Chung, E.-Y. Namkoong, T.-H. Kim, J. Org. Chem. 1995, 60, 4678-4679.
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Kang, S.-K.1
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Namkoong, E.-Y.4
Kim, T.-H.5
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15
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0028003856
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a) H. Pellissier, P.-Y. Michellys, M. Santelli, Tetrahedron Lett. 1994, 35, 6481-6484;
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(1994)
Tetrahedron Lett.
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Pellissier, H.1
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0030961403
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b) H. Pellissier, P.-Y. Michellys, M. Santelli, Tetrahedron 1997, 53, 7577-7586;
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Tetrahedron
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Pellissier, H.1
Michellys, P.-Y.2
Santelli, M.3
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0030744065
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c) H. Pellissier, P.-Y. Michellys, M. Santelli, Tetrahedron 1997, 53, 10733-10742.
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Tetrahedron
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Pellissier, H.1
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Santelli, M.3
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21
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33845375365
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Keinan has reported anti-Markovnikov regioselectivity in the Wacker oxidation of β-methylstyrenes, in this case due to the influence of heteroatoms: E. Keinan, K. K. Seth, R. Lamed, J. Am. Chem. Soc. 1986, 108, 3474-3480.
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J. Am. Chem. Soc.
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Keinan, E.1
Seth, K.K.2
Lamed, R.3
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22
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79957618467
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The mechanism of the Wacker reaction has been investigated mainly with ethene and higher homologues. There have been a small number of studies of the mechanism of the Wacker reaction of styrenes. These have been mainly carried out in largely aqueous media, see: a) L. M. Zakharova, M. N. Vargaftik, I. I. Moiseev, L. A. Katsman, Izv. Akad. Nauk SSSR Ser. Khim. 1970, 700-702:
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Izv. Akad. Nauk SSSR Ser. Khim.
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Zakharova, L.M.1
Vargaftik, M.N.2
Moiseev, I.I.3
Katsman, L.A.4
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24
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30744453688
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b) L. M. Zakharova, M. N. Vargaftik, I. I. Moiseev, L. A. Katsman, Kinet. Catal. 1969, 10, 901-903;
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Kinet. Catal.
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Zakharova, L.M.1
Vargaftik, M.N.2
Moiseev, I.I.3
Katsman, L.A.4
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25
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30744455389
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Kinet. Catal. 1969, 10, 736-744;
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(1969)
Kinet. Catal.
, vol.10
, pp. 736-744
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-
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27
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30744444846
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Kinet. Catal. 1989, 30, 1298-1299;
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(1989)
Kinet. Catal.
, vol.30
, pp. 1298-1299
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-
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30
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30744475382
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e) J. Vojtko, A. Kaszonyi, M. Cihová, M. Hrušovský, Collect. Czech. Chem. Commun. 1981, 46, 573-583;
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Collect. Czech. Chem. Commun.
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Vojtko, J.1
Kaszonyi, A.2
Cihová, M.3
Hrušovský, M.4
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33
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0009812403
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g) H. Okada, T. Noma, Y. Ketsuyama, H. Hashimoto, Bull. Chem. Soc. Jpn. 1968, 41, 1395-1400;
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Bull. Chem. Soc. Jpn.
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Okada, H.1
Noma, T.2
Ketsuyama, Y.3
Hashimoto, H.4
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35
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0000295212
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Unless otherwise started, product ratios were determined by gas chromatography (sec Experimental Section). Authentic samples of products 3a and 3b, necessary for calibration of the gas chromatography system, were produced by IBX oxidation of the corresponding commercial alcohols. See: a) M. Frigerio, M. Santagostino, S. Sputore, G. Palmisano, J. Org. Chem. 1995, 60, 7272-7727;
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Frigerio, M.1
Santagostino, M.2
Sputore, S.3
Palmisano, G.4
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37
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0033546262
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c) M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538.
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J. Org. Chem.
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Frigerio, M.1
Santagostino, M.2
Sputore, S.3
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38
-
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30744463821
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note
-
2). Conversion of the starting material was obviously lowered.
-
-
-
-
39
-
-
30744436737
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-
note
-
The reactions were carried out under a nitrogen atmosphere, in freeze-pump degassed solvents. In the presence of oxygen, the aldehyde products were found to be rapidly degraded to the analogous benzaldehydes. This reaction occurred even in the absence of palladium(II). but was markedly accelerated by the presence of the metal salt.
-
-
-
-
40
-
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30744452150
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note
-
2). The addition of external ligand sources, such as LiCl, also led to preferential formation of ketones.
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-
-
-
41
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30744458265
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a) M. Donati, D. Morelli, F. Conti, R. Ugo, Chim. Ind. 1968. 50, 231-235;
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Chim. Ind.
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Donati, M.1
Morelli, D.2
Conti, F.3
Ugo, R.4
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42
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0003433424
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b) F. Conti, M. Donati, G. F. Pregaglia, J. Organomet. Chem. 1971, 30, 421-429.
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Conti, F.1
Donati, M.2
Pregaglia, G.F.3
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45
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0037006827
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4 complex of styrene and rhodium has recently been isolated: H. Wadepohl, A. Metz, H. Pritzkow, Chem. Eur. J. 2002, 8, 1591-1602.
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Chem. Eur. J.
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Wadepohl, H.1
Metz, A.2
Pritzkow, H.3
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50
-
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30744478138
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-
note
-
The unknown quantity of water in the HPA makes exact stoichiometry difficult to assess.
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-
-
-
51
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0004055425
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Butterworth-Heinemann, Oxford
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W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 4th ed., Butterworth-Heinemann, Oxford, 2000.
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Purification of Laboratory Chemicals, 4th Ed.
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Armarego, W.L.F.1
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0005657603
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A. H. Schmidt, G. Kircher, J. Zylla, S. Veit, J. Chem. Soc. Perkin Trans. 1 1999, 409-414.
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Schmidt, A.H.1
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Zylla, J.3
Veit, S.4
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57
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85082724232
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K. Takeuchi, I. Kitagawa, F. Akiyama, T. Shibata, M. Kato, K. Okamoto, Synthesis 1987, 612-615.
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Synthesis
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Takeuchi, K.1
Kitagawa, I.2
Akiyama, F.3
Shibata, T.4
Kato, M.5
Okamoto, K.6
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59
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33845278073
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O. Farooq, M. Marcelli, G. K. S. Prakash, G. A. Olah, J. Am. Chem. Soc. 1988, 110 864-867.
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Farooq, O.1
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Olah, G.A.4
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61
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30744465243
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-
note
-
Cooling the neat alcohol in ice led to the liquid freezing.
-
-
-
-
62
-
-
30744437833
-
-
note
-
THF was used as the substrate was insoluble in neat DMF.
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-
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