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2 hydroboration conditions, but starting material was recovered.
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90
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0038739599
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note
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For example, when 2 reacted with 4-acetylphenyltriflate, after 8 h the major compound was 5a (isolated in 65% yield), and a reaction time of 18 h afforded a 70% of the 4-acetyltoluene 4a.
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93
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2 was used. For the preparation of this precatalyst, see: Hayashi, T.; Konishi, M. Kobori, Y.; Kumada, M.; Higuchi, T. Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
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To fully assess the reactivity of the iodoaryls, 4′-iodoacetophenone was also tested under similar conditions. No product was observed after 3 days, with a high proportion of acetophenone formation, showing the lack of reactivity in the transmetalation step, and subsequent protodehalogenation after prolonged heating.
-
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96
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0038739595
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note
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Spectroscopic and physical data of 4a-f, 4h, and 2j-k were identical to those of authentic samples available from Aldrich.
-
-
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97
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0038739597
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note
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2 was used. See ref 43.
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