1,5,7‐Triazabicyclo[4.4.0]dec‐1‐ene‐Mediated Acetylene Dicarboxylation and Alkyne Carboxylation Using Carbon Dioxide

Wang, Xi; Lim, Yu Na; Lee, Chan; Jang, Hye‐Young; Lee, Hyun Ju

doi:10.1002/ejoc.201201608

Cited by 49 publications

(11 citation statements)

References 78 publications

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“…Among them (Table S1 †), only 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) was effective (entry 4), suggesting that the reaction goes through the TBD-CO 2 intermediate pathway. 18 To prove the origin of the carboxylate, an isotope labeling experiment was performed. The carboxylation of 1a was conducted using labeled 13 CO 2 , and the 13 C-labeled product 2ac was obtained as shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions

Guo

Xie

et al. 2015

Green Chem.

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Silver tungstate was successfully developed as a bifunctional catalyst for the ligand-free carboxylation of various terminal alkynes with electron-withdrawing or electron-donating groups under atmospheric pressure of carbon dioxide (CO 2 ) at room temperature. In this protocol, dual activation -i.e., the terminal alkyne activated by silver, and CO 2 activation by the tungstate anion -was verified using nuclear magnetic resonance spectroscopy, and means that this reaction can be run under ambient conditions. Notably, this protocol can be applied to the preparation of a phenylacrylate derivative by a cascade reaction using phenylacetylene, CO 2 and benzylamine as starting materials.

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Section: Resultsmentioning

confidence: 99%

Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions

Guo

Xie

et al. 2015

Green Chem.

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“…The mechanism is proposed is that carboxylation is initiated by the formation of a TBD-CO 2 adduct, which undergoes the nucleophilic addition of acetylene producing a propynoate-TBD salt (Scheme 61). 69 Scheme 61 Metal-free carboxylation…”

Section: Metal-free Carboxylationmentioning

confidence: 99%

Recent Advances in Decarboxylative Reactions of Alkynoic Acids

Idris

Lee

2020

Synthesis

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Alkynoic acids have been widely employed as alkyne and alkene sources in decarboxylative reactions. Alkynoic acid coupling leads to the formation of direct coupling products and cyclized products through sequential reactions. Moreover, homocoupling and multicomponent reactions have been developed. The decarboxylative addition of alkynoic acids generates the corresponding alkene products. A number of synthetic methods are utilized for the preparation of arylpropynoic acids including the Sonogashira coupling and the carboxylation of terminal alkynes. Recently, the use of decarboxylative halogenations has also been reported. This review covers decarboxylative reactions of alkynoic acids reported between 2013 and 2019; further, it is divided into several sections according to the type of reaction.1 Introduction2 Direct Coupling3 Sequential Reactions4 Homocoupling5 Multicomponent Reactions6 Addition7 Halogenations8 Synthesis of Alkynoic Acids9 Conclusion

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“…Direct carboxylation of acetylene with CO 2 in the presence of 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) led to acetylene dicarboxylic acid derivatives ( Scheme 88 ) [ 199 ].…”

Section: Acetylene In Organic Synthesismentioning

confidence: 99%

Acetylene in Organic Synthesis: Recent Progress and New Uses

et al. 2018

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Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule.

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1,5,7‐Triazabicyclo[4.4.0]dec‐1‐ene‐Mediated Acetylene Dicarboxylation and Alkyne Carboxylation Using Carbon Dioxide

Abstract: The free acids are obtained by chromatography of the carboxylate salts.

Cited by 49 publications

References 78 publications

Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions

Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions

Recent Advances in Decarboxylative Reactions of Alkynoic Acids

Acetylene in Organic Synthesis: Recent Progress and New Uses

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1,5,7‐Triazabicyclo[4.4.0]dec‐1‐ene‐Mediated Acetylene Dicarboxylation and Alkyne Carboxylation Using Carbon Dioxide

Abstract: The free acids are obtained by chromatography of the carboxylate salts.

Cited by 49 publications

References 78 publications

Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO2 in ambient conditions

Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO2 in ambient conditions

Recent Advances in Decarboxylative Reactions of Alkynoic Acids

Acetylene in Organic Synthesis: Recent Progress and New Uses

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Product

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Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions

Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions