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 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. • In-situ generated PPh 2 -ImPy-Ni(0) catalysts demonstrated structural rigidity and stability. • The catalysts achieved a turnover number (TON) of 570 with 82% yield for the synthesis of acrylates from ethylene and CO 2 . • The catalysts addressed the typical trade-off between TON and yield seen in previous studies, maintaining high efficiency and yield. • Sodium acrylate was successfully isolated via a simple extraction process, demonstrating practical applicability.

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Publication Details

Journal
Journal of CO2 Utilization
Published
2024-12-18
DOI
https://doi.org/10.1016/j.jcou.2024.103004
Citations
3
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
Field-Weighted Citation Impact
0.53
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article

In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2

Seongwook Park, Huijeong Ryu, Wooyong Seong, Woosong Han et al.
3 citations
Journal of CO2 Utilization
Carbon dioxide utilization in catalysis
0.53
article

In situ generated diphenylphosphine-chelated imidazo[1,5-a]pyridin-3-ylidene nickel(0) catalysts for highly efficient acrylate synthesis from ethylene and CO2

Seongwook Park, Huijeong Ryu, Wooyong Seong, Woosong Han, Sukwon Hong, Da-Ae Park, Kyung‐Ho Park, Jiyun Kim, Changmuk Kang, Chang‐Hee Lee, Seyong Kim, Hyun Tae Kim, Hyun Min Park
article en
3 citations

Abstract

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. • In-situ generated PPh 2 -ImPy-Ni(0) catalysts demonstrated structural rigidity and stability. • The catalysts achieved a turnover number (TON) of 570 with 82% yield for the synthesis of acrylates from ethylene and CO 2 . • The catalysts addressed the typical trade-off between TON and yield seen in previous studies, maintaining high efficiency and yield. • Sodium acrylate was successfully isolated via a simple extraction process, demonstrating practical applicability.

Journal of CO2 UtilizationVol. 91
Gwangju Institute of Science and Technology (KR), LG (South Korea) (KR)
Openalex Percentile: Top 44%
Carbon dioxide utilization in catalysis
0.53
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