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4
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For palladium-catalyzed allylic alkylation of α-sulfonyl activated carbanions, see: (a) Giambastiani, G.; Poli, G. J. Org. Chem. 1998, 63, 9608.
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For palladium-catalyzed allylic alkylation of α-sulfenyl activated carbanions, see: (d) Hiroi, K.; Hidaka, A.; Sezaki, R.; Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769.
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Hidaka, A.2
Sezaki, R.3
Imamura, Y.4
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9
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33947094963
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To our knowledge, only two examples in the literature report the use of α-sulfinyl carbanions as nucleophilic partners in Pd-mediated allylic alkylation. For a stoichiometric example see: (a) Trost, B. M.; Weber, L.; Strege, P.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3426.
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Weber, L.2
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Fullerton, T.J.4
Dietsche, T.J.5
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(b) For a catalytic example see: Hiroi, K.; Suzuki, Y.; Kato, F.; Kyo, Y. Tetrahedron: Asymmetry 2001, 12, 37.
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Hiroi, K.1
Suzuki, Y.2
Kato, F.3
Kyo, Y.4
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11
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For reviews concerning the use of sulfoxide ligands in palladiumcatalysis, see: (a) Fernandez, I.; Khiar, N. Chem. Rev. 2003, 103, 3651.
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(b) Hanquet, G.; Colobert, F.; Lanners, S.; Solladié, G. ARKIVOC 2003, (vii), 328.
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Colobert, F.2
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Poli, G.; Giambastiani, G.; Pacini, B.; Porcelloni, M. J. Org. Chem. 1998, 63, 804.
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Giambastiani, G.2
Pacini, B.3
Porcelloni, M.4
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PhD Thesis; University Pierre et Marie Curie: Paris
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Giambastiani, G. PhD Thesis; University Pierre et Marie Curie: Paris, 2001.
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Madec, D.; Prestat, G.; Martini, E.; Fristrup, P.; Poli, G.; Norrby, P.-O. Org. Lett. 2005, 7, 995.
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Prestat, G.2
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Poli, G.5
Norrby, P.-O.6
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16
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33646553813
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see ref. 8b. see ref. 8c
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(a) This substrate was prepared by oxidation of the corresponding thioether (see ref. 8b) with Oxone® and wet alumina (see ref. 8c).
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17
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0001323925
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(b) Babin, D.; Demassey, J.; Demoute, J.-P.; Dutheil, P.; Terrie, I.; Tessier, J. J. Org. Chem. 1992, 57, 584.
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Tessier, J.6
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Chapman and Hall: New York
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(c) Starks, C. M.; Liotta, C. L.; Halpern, M. Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives; Chapman and Hall: New York, 1994.
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Liotta, C.L.2
Halpern, M.3
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23
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33646592453
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note
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4 and the solvent was removed in vacuo. The crude product was purified by flash chromatography.
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24
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Nokami, J.; Kataoka, K.; Shiraishi, K.; Osafune, M.; Hussain, I.; Sumida, S.-I. J. Org. Chem. 2001, 66, 1228.
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Sumida, S.-I.6
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Ono, T.; Tamaoka, T.; Yuasa, Y.; Matsuda, T.; Nokami, J.; Wakabayashi, S. J. Am. Chem. Soc. 1984, 106, 7890.
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Wakabayashi, S.6
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26
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33646594347
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see ref. 8
-
This substrate has been prepared by oxidation of the corresponding thioether with Oxone® and wet alumina (see ref. 8).
-
-
-
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27
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33646544969
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PhD Thesis; Université Pierre et Marie Curie: Paris
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Brebion, F. PhD Thesis; Université Pierre et Marie Curie: Paris, 2004.
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Trost, B.M.1
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Hiroi, K.3
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33
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33646572147
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a values of compounds strictly related to 1f and 1h see: http://www.chem.wisc.edu/areas/reich/pkatable/.
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34
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0037870789
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Xu, L.; Cheng, J.; Trudell, M. L. J. Org. Chem. 2003, 68, 5388.
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