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Sambasivarao, K.1
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6
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(a) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
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Miyaura, N.1
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Miyaura, N.1
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Darses, S.1
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30
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0242427870
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note
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Isomer 4 was isolated in 18% yield for the aliphatic Baylis-Hillman reagent (Table 1, entry 4).
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0026530228
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Wang, S.-Z.; Yamamoto, K.; Yamada, H.; Takahashi, T. Tetrahedron 1992, 48, 2333.
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Wang, S.-Z.1
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Takahashi, T.4
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34
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0031585063
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Basavaiah, D.1
Krishnamacharyulu, M.2
Suguna, H.R.3
Pandiaraju, S.4
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35
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0037195743
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Similar selectivity was observed in the Suzuki cross-coupling of potassium alkenyltrifluoroborates: Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424.
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Molander, G.A.1
Bernardi, C.R.2
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36
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0034600318
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It is interesting to note that trifluoroborate reagents have been shown to be ineffective in Suzuki coupling reactions with certain catalyst systems. See: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
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J. Am. Chem. Soc.
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Littke, A.F.1
Dai, C.2
Fu, G.C.3
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37
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0242511317
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note
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2 is added to a solution of potassium organotrifluoroborate salt 2 (1 mmol) in methanol (5 mL) at 0°C under a nitrogen atmosphere. The reaction mixture is allowed to stir at room temperaure until completion (TLC monitoring). The mixture is then diluted with diethyl ether (10 mL) and filtered to remove solids. The solvent is removed under reduced pressure and the product purified by chromatography (silica gel) to afford analytically pure product.
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