In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2
Diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene (PPh₂-ImPy) nickel(0) catalysts were synthesized in-situ from imidazolium salts and various commercially available nickel(0) complexes using a base. These catalysts exhibited a highly planar and rigid structure, as confirmed by X-ray crystal...
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| Format: | Article |
| Language: | English |
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Elsevier
2025-01-01
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| Series: | Journal of CO2 Utilization |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2212982024003391 |
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| author | Changmuk Kang Seyong Kim Woosong Han Huijeong Ryu Wooyong Seong Jiyun Kim Da-Ae Park Seongwook Park Kyungho Park Hyun Min Park Hyun Tae Kim Chang Hee Lee Sukwon Hong |
| author_facet | Changmuk Kang Seyong Kim Woosong Han Huijeong Ryu Wooyong Seong Jiyun Kim Da-Ae Park Seongwook Park Kyungho Park Hyun Min Park Hyun Tae Kim Chang Hee Lee Sukwon Hong |
| author_sort | Changmuk Kang |
| collection | DOAJ |
| description | Diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene (PPh₂-ImPy) nickel(0) catalysts were synthesized in-situ from imidazolium salts and various commercially available nickel(0) complexes using a base. These catalysts exhibited a highly planar and rigid structure, as confirmed by X-ray crystallographic analysis. Remarkably, the in-situ generated PPh₂-ImPy-Ni(0) catalyst demonstrated a turnover number (TON) of 570 while maintaining a high yield of 82 %, overcoming the typical trade-off between TON and yield often observed in acrylate synthesis reactions, where the use of excess base to achieve high TON typically results in lower product yields. Moreover, the ligand precursors (PPh₂-ImPy∙HCl salts) were stable under open-air conditions, making them easy to handle. The in-situ generation protocol using the ligand precursors and commercially available metal sources, eliminates the need for synthesizing sensitive Ni(0) catalysts. Furthermore, the sodium acrylate product was efficiently isolated from the reaction mixture through a straightforward extraction process. |
| format | Article |
| id | doaj-art-80b9aad9955a42c98e8cda2f4bbbb2cd |
| institution | Kabale University |
| issn | 2212-9839 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of CO2 Utilization |
| spelling | doaj-art-80b9aad9955a42c98e8cda2f4bbbb2cd2025-01-13T04:18:50ZengElsevierJournal of CO2 Utilization2212-98392025-01-0191103004In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2Changmuk Kang0Seyong Kim1Woosong Han2Huijeong Ryu3Wooyong Seong4Jiyun Kim5Da-Ae Park6Seongwook Park7Kyungho Park8Hyun Min Park9Hyun Tae Kim10Chang Hee Lee11Sukwon Hong12Department of Chemistry, Gwangju Institute of Science and Technology, 123, Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of KoreaDepartment of Chemistry, Gwangju Institute of Science and Technology, 123, Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of KoreaDepartment of Chemistry, Gwangju Institute of Science and Technology, 123, Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of KoreaDepartment of Chemistry, Gwangju Institute of Science and Technology, 123, Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of KoreaDepartment of Chemistry, Gwangju Institute of Science and Technology, 123, Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of KoreaDepartment of Chemistry, Gwangju Institute of Science and Technology, 123, Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of KoreaPlatform Technology Research Center, LG Chem. LTD., E7 Block LG Science Park, 30, Magokjungang 10-ro, Gangseo-gu, Seoul 07796, Republic of KoreaPlatform Technology Research Center, LG Chem. LTD., E7 Block LG Science Park, 30, Magokjungang 10-ro, Gangseo-gu, Seoul 07796, Republic of KoreaPlatform Technology Research Center, LG Chem. LTD., E7 Block LG Science Park, 30, Magokjungang 10-ro, Gangseo-gu, Seoul 07796, Republic of KoreaPlatform Technology Research Center, LG Chem. LTD., E7 Block LG Science Park, 30, Magokjungang 10-ro, Gangseo-gu, Seoul 07796, Republic of KoreaPlatform Technology Research Center, LG Chem. LTD., E7 Block LG Science Park, 30, Magokjungang 10-ro, Gangseo-gu, Seoul 07796, Republic of KoreaPlatform Technology Research Center, LG Chem. LTD., E7 Block LG Science Park, 30, Magokjungang 10-ro, Gangseo-gu, Seoul 07796, Republic of Korea; Corresponding authors.Department of Chemistry, Gwangju Institute of Science and Technology, 123, Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of Korea; Corresponding authors.Diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene (PPh₂-ImPy) nickel(0) catalysts were synthesized in-situ from imidazolium salts and various commercially available nickel(0) complexes using a base. These catalysts exhibited a highly planar and rigid structure, as confirmed by X-ray crystallographic analysis. Remarkably, the in-situ generated PPh₂-ImPy-Ni(0) catalyst demonstrated a turnover number (TON) of 570 while maintaining a high yield of 82 %, overcoming the typical trade-off between TON and yield often observed in acrylate synthesis reactions, where the use of excess base to achieve high TON typically results in lower product yields. Moreover, the ligand precursors (PPh₂-ImPy∙HCl salts) were stable under open-air conditions, making them easy to handle. The in-situ generation protocol using the ligand precursors and commercially available metal sources, eliminates the need for synthesizing sensitive Ni(0) catalysts. Furthermore, the sodium acrylate product was efficiently isolated from the reaction mixture through a straightforward extraction process.http://www.sciencedirect.com/science/article/pii/S2212982024003391N-heterocyclic carbeneNickelAcrylateEthyleneCarbon dioxide |
| spellingShingle | Changmuk Kang Seyong Kim Woosong Han Huijeong Ryu Wooyong Seong Jiyun Kim Da-Ae Park Seongwook Park Kyungho Park Hyun Min Park Hyun Tae Kim Chang Hee Lee Sukwon Hong In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2 Journal of CO2 Utilization N-heterocyclic carbene Nickel Acrylate Ethylene Carbon dioxide |
| title | In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2 |
| title_full | In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2 |
| title_fullStr | In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2 |
| title_full_unstemmed | In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2 |
| title_short | In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2 |
| title_sort | in situ generated diphenylphosphine chelated imidazo 1 5 a pyridin 3 ylidene nickel 0 catalysts for highly efficient acrylate synthesis from ethylene and co2 |
| topic | N-heterocyclic carbene Nickel Acrylate Ethylene Carbon dioxide |
| url | http://www.sciencedirect.com/science/article/pii/S2212982024003391 |
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