Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel
Palladium catalysts deposited over silica gel bearing simple amine (≡Si(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub>) and composite functional amide pendants equipped with various donor groups in the terminal position (≡Si(CH<sub>2</sub>)<sub>3</...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-10-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/10/10/1186 |
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| author | Miloslav Semler Filip Horký Petr Štěpnička |
| author_facet | Miloslav Semler Filip Horký Petr Štěpnička |
| author_sort | Miloslav Semler |
| collection | DOAJ |
| description | Palladium catalysts deposited over silica gel bearing simple amine (≡Si(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub>) and composite functional amide pendants equipped with various donor groups in the terminal position (≡Si(CH<sub>2</sub>)<sub>3</sub>NHC(O)CH<sub>2</sub>Y, Y = SMe, NMe<sub>2</sub> and PPh<sub>2</sub>) were prepared and evaluated in Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes to give 1,3-disubstituted prop-2-yn-1-ones. Generally, the catalysts showed good catalytic activity in the reactions of aroyl chlorides with aryl alkynes under relatively mild reaction conditions even without adding a copper co-catalyst. However, their repeated use was compromised by a significant loss of activity after the first catalytic run. |
| first_indexed | 2024-03-10T15:37:36Z |
| format | Article |
| id | doaj.art-861f92fa03a34364a2415302881d8855 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T15:37:36Z |
| publishDate | 2020-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-861f92fa03a34364a2415302881d88552023-11-20T17:08:25ZengMDPI AGCatalysts2073-43442020-10-011010118610.3390/catal10101186Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica GelMiloslav Semler0Filip Horký1Petr Štěpnička2Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech RepublicDepartment of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech RepublicDepartment of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech RepublicPalladium catalysts deposited over silica gel bearing simple amine (≡Si(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub>) and composite functional amide pendants equipped with various donor groups in the terminal position (≡Si(CH<sub>2</sub>)<sub>3</sub>NHC(O)CH<sub>2</sub>Y, Y = SMe, NMe<sub>2</sub> and PPh<sub>2</sub>) were prepared and evaluated in Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes to give 1,3-disubstituted prop-2-yn-1-ones. Generally, the catalysts showed good catalytic activity in the reactions of aroyl chlorides with aryl alkynes under relatively mild reaction conditions even without adding a copper co-catalyst. However, their repeated use was compromised by a significant loss of activity after the first catalytic run.https://www.mdpi.com/2073-4344/10/10/1186deposited catalystspalladiumfunctional amidesSonogashira reactionalkynyl ketone synthesis |
| spellingShingle | Miloslav Semler Filip Horký Petr Štěpnička Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel Catalysts deposited catalysts palladium functional amides Sonogashira reaction alkynyl ketone synthesis |
| title | Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel |
| title_full | Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel |
| title_fullStr | Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel |
| title_full_unstemmed | Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel |
| title_short | Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel |
| title_sort | synthesis of alkynyl ketones by sonogashira cross coupling of acyl chlorides with terminal alkynes mediated by palladium catalysts deposited over donor functionalized silica gel |
| topic | deposited catalysts palladium functional amides Sonogashira reaction alkynyl ketone synthesis |
| url | https://www.mdpi.com/2073-4344/10/10/1186 |
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