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For use of aryl mesylates as partners in cross-coupling reactions see: a
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For use of aryl mesylates as partners in cross-coupling reactions see: (a) Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531.
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Percec, V.1
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(d) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1066.
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(e) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895.
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(f) Ueda, M.; Saitoh, A.; Oh-tani, S.; Miyuara, N. J. Org. Chem. 1997, 62, 8024.
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(g) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem. 2004, 69, 3447.
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(b) Cai, C.; Rivera, N. R.; Balsells, J.; Sidler, R. R.; McWilliams, J. C.; Schultz, C. S.; Sun, Y. Org. Lett. 2006, 8, 5161.
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Cai, C.1
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23
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40949089148
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Available from Nippon Chemical Co. (catalogue no. 103099-52-1).
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Available from Nippon Chemical Co. (catalogue no. 103099-52-1).
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24
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40949109064
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See Supporting Information for details of butoxyesterification of 4-t- butylphenyltosylate with other bases and solvents
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See Supporting Information for details of butoxyesterification of 4-t- butylphenyltosylate with other bases and solvents.
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25
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0042693206
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Substrates with certain electron-withdrawing groups (e.g., 3-cyanophenyl methanesulfonate) were transformed into mixtures of butyl ether and ester when the reaction was carried out in DMSO. Ether formation occurred without ligand and Pd in DMSO presumably via a base-mediated sulfonyl transfer mechanism: sulfonyl transfer occurs to form primary sulfonate and phenol, and phenol displaces primary sulfonate in the presence of base. This has been observed previously: Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11253. This transformation was completely suppressed when the reaction was conducted in toluene or dioxane at 100°C.
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Substrates with certain electron-withdrawing groups (e.g., 3-cyanophenyl methanesulfonate) were transformed into mixtures of butyl ether and ester when the reaction was carried out in DMSO. Ether formation occurred without ligand and Pd in DMSO presumably via a base-mediated sulfonyl transfer mechanism: sulfonyl transfer occurs to form primary sulfonate and phenol, and phenol displaces primary sulfonate in the presence of base. This has been observed previously: Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11253. This transformation was completely suppressed when the reaction was conducted in toluene or dioxane at 100°C.
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