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This work was partly presented in the 88th Annual Meeting of Chemical Society of Japan, March 2008, 2H332. An analogous copper-catalyzed carboxylation of aryl- or alkenylboronic esters with CO2 was reported by Prof. Hou's group at the same meeting. See: Ohishi, T, Hou, Z. The 88th Annual Meeting of Chemical Society of Japan, March 2008, 2H333. We would like to thank Prof. Hou for discussion on this subject
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2 was reported by Prof. Hou's group at the same meeting. See: Ohishi, T.; Hou, Z. The 88th Annual Meeting of Chemical Society of Japan, March 2008, 2H333. We would like to thank Prof. Hou for discussion on this subject.
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The active catalyst seemed to be sensitive to water and oxygen in the air and decrease of the yield of carboxylation product was often observed in the reaction under 1 atm CO2 with a balloon. A closed system can achieve good reproducibility
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2 with a balloon. A closed system can achieve good reproducibility.
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29
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59949087976
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Other solvent such as toluene, 1,4-dioxane, and acetonitrile resulted in low conversion and only a trace amount of carboxylation product was obtained
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Other solvent such as toluene, 1,4-dioxane, and acetonitrile resulted in low conversion and only a trace amount of carboxylation product was obtained.
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Generality of the reaction was examined with 5 mol % of CuI at 90 °C to shorten the reaction time.
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Generality of the reaction was examined with 5 mol % of CuI at 90 °C to shorten the reaction time.
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The reaction did not proceed without CsF. Concerning the effect of CsF, promotion of the transmetalation step by forming arylfluoroborates would be most likely although participation in the carboxylation step by making fluorocuprate might also be possible. Research is now in progress to elucidate the mechanism including the role of CsF and also of the oxazoline ligand
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The reaction did not proceed without CsF. Concerning the effect of CsF, promotion of the transmetalation step by forming arylfluoroborates would be most likely although participation in the carboxylation step by making fluorocuprate might also be possible. Research is now in progress to elucidate the mechanism including the role of CsF and also of the oxazoline ligand.
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