- Kinetic Analysis as an Optimization Tool for Catalytic Esterification with a Moisture-Tolerant Zirconium Complex
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This work describes the use of kinetics as a tool for rational optimization of an esterification process with down to equimolar ratios of reagents using a recyclable commercially available zirconocene complex in catalytic amounts. In contrast to previously reported group IV metal-catalyzed esterification protocols, the work presented herein circumvents the use of water scavengers and perfluorooctane sulfonate (PFOS) ligands. Insights into the operating mechanism are presented.
- Dalla-Santa, Oscar,Lundberg, Helena,Szabó, Zoltán,Villo, Piret
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p. 6959 - 6969
(2020/06/27)
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- Development of triazine-based esterifying reagents containing pyridines as a nucleophilic catalyst
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We have developed new triazine-based esterifying reagents comprising pyridines that can act as a nucleophilic catalyst. 1-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-3,5-lutidinium chloride (DMT-3,5-LUT) was found to exhibit a superior reactivity for the dehydrating condensation reaction between carboxylic acids and alcohols. The reaction of DMT-3,5-LUT with carboxylic acids produces intermediacy of acyloxytriazines, which is known to exhibit moderate reactivity toward alcohols, with concomitant liberation of 3,5-lutidine. The subsequent chemical transformation of the acyloxytriazines and alcohols into esters can be accelerated by the action of 3,5-lutidine as a nucleophilic catalyst. The detailed reaction mechanism revealed by a time-course analysis of the reactions is also discussed.
- Yamada, Kohei,Liu, Jie,Kunishima, Munetaka
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supporting information
p. 6569 - 6575
(2018/09/25)
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- A nucleophilic Fe catalyst for transesterifications under neutral conditions
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Carboxylic esters belong to the most important functional groups in organic chemistry. Strong efforts have been made in developing mild catalytic procedures for their preparation. Among the various methods developed to date, transesterifications have occupied an important space. In the present paper, a new catalytic method for this process based on the use of nucleophilic Fe(-II) complexes is presented. Evidence for the formation of an intermediate acyl Fe complex will be presented as well as investigations on scope and limitations.
- Magens, Silja,Ertelt, Melanie,Jatsch, Anja,Plietker, Bernd
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- Synthesis of caffeic acid esters
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A new method for the preparation of caffeic acid esters was investigated. Ten caffeic acid esters were prepared by condensation of protocatechualdehyde with malonic acid mono-esters in moderate yield. Malonic acid mono-esters were prepared from the corresponding malonate di-esters. The conformations of compounds are trans (E) form.
- Xia, Chun-Nian,Hu, Wei-Xiao
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p. 332 - 334
(2007/10/03)
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- Ligand-induced acceleration of the intramolecular [3 + 2] cycloaddition between alkynes and alkylidenecyclopropanes
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(Chemical Equation Presented) Bulky phosphite L6 and several sterically robust phosphoramidites are excellent ligands for promoting the Pd-catalyzed [3 + 2] intramolecular cycloaddition between alkylidenecyclopropanes and alkynes. The use of th
- Duran, Juan,Gulias, Moises,Castedo, Luis,Mascarenas, Jose L.
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p. 5693 - 5696
(2007/10/03)
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