Gold Catalysis of Non-Conjugated Haloacetylenes

Siera, Hannah; Semleit, Nina; Kreuzahler, Mathis; Wölper, Christoph; Haberhauer, Gebhard

doi:10.1055/s-0040-1706606

Cited by 2 publications

(1 citation statement)

References 39 publications

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“…Taking into account these requirements, as well as the fact that catalysis based on gold is rapidly developing in the 21st century, which is indicated in [14,15], this suggests that it is expedient to conduct a study on the use of catalysts based on gold with ligands of the triphenylphosphine type in the process of catalytic hydration of acetylene, as indicated in [16,17]. Considering all of the above, the problem of finding a catalyst for the hydration reaction that will work at atmospheric pressure and will not be toxic, but at the same time be hydrophilic and reproducible, is an urgent problem.…”

Section: Literature Review and Problem Statementmentioning

confidence: 99%

Preparation of aurum chloride complex and its use for industrial acetylene hydration catalyst process

Kokhan

Kudryavtsev

Merzhyievskyi

2022

EEJET

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The use of a modern homogeneous metal complex catalyst for the hydration of acetylenes is being investigated. The process is relevant both for the industry of basic organic synthesis and for the perfume industry. The analysis of existing processes used in industry for the production of acetaldehyde was carried out. Significant shortcomings of existing processes are revealed: low environmental friendliness and high energy consumption. To solve this problem, the reaction of hydration of an acetylene compound was studied using a modern homogeneous catalyst based on gold, which is not toxic. The study was conducted by selecting aliquots during the reaction. Using the 1H NMR spectroscopy method, the conversion values of phenylacetylene were calculated for the time values corresponding to the moments of aliquot sampling. The reaction order with respect to phenylacetylene was calculated and the reaction constant under the reaction conditions was calculated. When reacting in the presence of the proposed catalyst, a conversion of phenylacetylene of 86.96 % is achieved in 3 hours. The data obtained provide grounds for carrying out the process of catalytic hydration of acetylenes, namely phenylacetylene, with the production of acetophenone, which is important for use in the perfume industry. The data obtained can be applied to the process of hydration of acetylene with the formation of acetaldehyde, which is widely used in the industry of basic organic synthesis. For the process of catalytic hydration of acetylene compounds, a hardware design is proposed, a gas-liquid reactor with a changing hydrodynamic situation, which, together with the product separation column, is combined into a single installation. Using an optimized method, a catalyst based on gold chloride was synthesized from a gold alloy.

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Section: Literature Review and Problem Statementmentioning

confidence: 99%

Preparation of aurum chloride complex and its use for industrial acetylene hydration catalyst process

Kokhan

Kudryavtsev

Merzhyievskyi

2022

EEJET

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Regio‐ and Stereoselective Synthesis of Ynenamides through Gold(I)‐Catalyzed Hydroalkynylation of Ynamides

et al. 2022

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Transition metal catalysis is a useful tool for C−C bond‐forming reactions. Of special interest is the hydroalkynylation reaction of alkynes, which provides a simple method for the synthesis of enynes representing interesting structural motifs in organic chemistry. So far, there are only a few examples of gold(I)‐catalyzed hydroalkynylation reactions. Herein, we were able to show experimentally that the gold(I)‐catalyzed hydroalkynylation of ynamides leads regio‐ and stereoselectively to the corresponding ynenamides, a rather unknown type of molecule. A wide range of products could be generated with yields up to 90 % and, in contrast to many other gold‐catalyzed alkyne dimerization reactions, alkyl groups are tolerated. Quantum chemical calculations and NMR labelling experiments reveal a mechanism via dual gold catalysis.

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Gold Catalysis of Non-Conjugated Haloacetylenes

Cited by 2 publications

References 39 publications

Preparation of aurum chloride complex and its use for industrial acetylene hydration catalyst process

Preparation of aurum chloride complex and its use for industrial acetylene hydration catalyst process

Regio‐ and Stereoselective Synthesis of Ynenamides through Gold(I)‐Catalyzed Hydroalkynylation of Ynamides

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