“TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation
A recently published article by our research group demonstrated that the hydrothiolation of activated alkynes is a successful way to functionalize thiols bearing catechols. The reaction was promoted by the CuNPs/TiO<sub>2</sub> nanocatalyst and was regio- and stereoselective towards the...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-11-01
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| Series: | Chemistry Proceedings |
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| Online Access: | https://www.mdpi.com/2673-4583/12/1/4 |
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| author | Matías Capurso Gabriel Radivoy Fabiana Nador Viviana Dorn |
| author_facet | Matías Capurso Gabriel Radivoy Fabiana Nador Viviana Dorn |
| author_sort | Matías Capurso |
| collection | DOAJ |
| description | A recently published article by our research group demonstrated that the hydrothiolation of activated alkynes is a successful way to functionalize thiols bearing catechols. The reaction was promoted by the CuNPs/TiO<sub>2</sub> nanocatalyst and was regio- and stereoselective towards the <i>anti</i>-Markovnikov <i>Z</i>-vinyl sulfide with good to excellent yields (47–97%). The scope of the reaction was evaluated and, based on experimental observations, the reaction mechanism was investigated through DFT studies. Theoretical results and experimental data were consistent with a reaction mechanism based on a copper-catalyzed <i>anti</i>-Markovnikov hydrothiolation process that favors the formation of the <i>Z</i>-vinyl sulfide. |
| first_indexed | 2024-03-11T02:37:41Z |
| format | Article |
| id | doaj.art-3aee6b7fac1e4614b7b71981b749fae9 |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T02:37:41Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj.art-3aee6b7fac1e4614b7b71981b749fae92023-11-18T09:47:40ZengMDPI AGChemistry Proceedings2673-45832022-11-01121410.3390/ecsoc-26-13588“TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT CalculationMatías Capurso0Gabriel Radivoy1Fabiana Nador2Viviana Dorn3Instituto de Química del Sur (INQUISUR-CONICET), Departamento de Química, Universidad Nacional del Sur, Av. Alem 1253, Bahía Blanca B8000CPB, ArgentinaInstituto de Química del Sur (INQUISUR-CONICET), Departamento de Química, Universidad Nacional del Sur, Av. Alem 1253, Bahía Blanca B8000CPB, ArgentinaInstituto de Química del Sur (INQUISUR-CONICET), Departamento de Química, Universidad Nacional del Sur, Av. Alem 1253, Bahía Blanca B8000CPB, ArgentinaInstituto de Química del Sur (INQUISUR-CONICET), Departamento de Química, Universidad Nacional del Sur, Av. Alem 1253, Bahía Blanca B8000CPB, ArgentinaA recently published article by our research group demonstrated that the hydrothiolation of activated alkynes is a successful way to functionalize thiols bearing catechols. The reaction was promoted by the CuNPs/TiO<sub>2</sub> nanocatalyst and was regio- and stereoselective towards the <i>anti</i>-Markovnikov <i>Z</i>-vinyl sulfide with good to excellent yields (47–97%). The scope of the reaction was evaluated and, based on experimental observations, the reaction mechanism was investigated through DFT studies. Theoretical results and experimental data were consistent with a reaction mechanism based on a copper-catalyzed <i>anti</i>-Markovnikov hydrothiolation process that favors the formation of the <i>Z</i>-vinyl sulfide.https://www.mdpi.com/2673-4583/12/1/4hydrothiolationDFTcomputational chemistry |
| spellingShingle | Matías Capurso Gabriel Radivoy Fabiana Nador Viviana Dorn “TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation Chemistry Proceedings hydrothiolation DFT computational chemistry |
| title | “TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation |
| title_full | “TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation |
| title_fullStr | “TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation |
| title_full_unstemmed | “TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation |
| title_short | “TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation |
| title_sort | tyc reaction between alkynes and catechol thiol derivatives prompted by metal nanocatalysis mechanism study by dft calculation |
| topic | hydrothiolation DFT computational chemistry |
| url | https://www.mdpi.com/2673-4583/12/1/4 |
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