Investigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculations
Abstract Metal or metal cluster-doped zeolites catalyse a wide variety of reactions. In this work, a coupling reaction between bromobenzene and phenylboronic acid to yield biphenyl with the Pd–H-Beta zeolite catalyst was investigated with density functional theory (DFT) calculations. Utilizing a mod...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2024-01-01
|
| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-51116-x |
| _version_ | 1797363475895287808 |
|---|---|
| author | Bundet Boekfa Thana Maihom Masahiro Ehara Jumras Limtrakul |
| author_facet | Bundet Boekfa Thana Maihom Masahiro Ehara Jumras Limtrakul |
| author_sort | Bundet Boekfa |
| collection | DOAJ |
| description | Abstract Metal or metal cluster-doped zeolites catalyse a wide variety of reactions. In this work, a coupling reaction between bromobenzene and phenylboronic acid to yield biphenyl with the Pd–H-Beta zeolite catalyst was investigated with density functional theory (DFT) calculations. Utilizing a model system with tetrahedral Pd4 clusters within the H-Beta zeolite, it was demonstrated that the catalyst exhibited notable reactivity by effectively reducing the activation energy barrier for the reaction. Our investigation revealed that the zeolite framework facilitated electron transfer to the Pd cluster, thereby increasing the reaction activity. The coupling reaction was shown to be exothermic and comprise three main steps: oxidative addition of bromobenzene (C6H5Br), transmetallation with phenylboronic acid (C6H5B(OH)2), and reductive elimination of biphenyl (C12H10). Specifically, in the transmetallation step, which was the rate-determining step, the C–B bond breaking in phenylboronic acid (C6H5B(OH)2) and the phenylboronate anion (C6H5B(OH)3 –) were compared under neutral and basic conditions, respectively. This comprehensive study clarifies the mechanism for the reaction with the modified Pd zeolite catalyst and highlights the essential role of the zeolite framework. |
| first_indexed | 2024-03-08T16:21:53Z |
| format | Article |
| id | doaj.art-ebf31e61d77a4d4c8a365ee3d64af182 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-03-08T16:21:53Z |
| publishDate | 2024-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-ebf31e61d77a4d4c8a365ee3d64af1822024-01-07T12:20:13ZengNature PortfolioScientific Reports2045-23222024-01-011411910.1038/s41598-023-51116-xInvestigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculationsBundet Boekfa0Thana Maihom1Masahiro Ehara2Jumras Limtrakul3Division of Chemistry, Department of Physical and Material Sciences, Faculty of Liberal Arts and Science, Kasetsart UniversityDivision of Chemistry, Department of Physical and Material Sciences, Faculty of Liberal Arts and Science, Kasetsart UniversityInstitute for Molecular ScienceDepartment of Materials Science and Engineering, School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and TechnologyAbstract Metal or metal cluster-doped zeolites catalyse a wide variety of reactions. In this work, a coupling reaction between bromobenzene and phenylboronic acid to yield biphenyl with the Pd–H-Beta zeolite catalyst was investigated with density functional theory (DFT) calculations. Utilizing a model system with tetrahedral Pd4 clusters within the H-Beta zeolite, it was demonstrated that the catalyst exhibited notable reactivity by effectively reducing the activation energy barrier for the reaction. Our investigation revealed that the zeolite framework facilitated electron transfer to the Pd cluster, thereby increasing the reaction activity. The coupling reaction was shown to be exothermic and comprise three main steps: oxidative addition of bromobenzene (C6H5Br), transmetallation with phenylboronic acid (C6H5B(OH)2), and reductive elimination of biphenyl (C12H10). Specifically, in the transmetallation step, which was the rate-determining step, the C–B bond breaking in phenylboronic acid (C6H5B(OH)2) and the phenylboronate anion (C6H5B(OH)3 –) were compared under neutral and basic conditions, respectively. This comprehensive study clarifies the mechanism for the reaction with the modified Pd zeolite catalyst and highlights the essential role of the zeolite framework.https://doi.org/10.1038/s41598-023-51116-x |
| spellingShingle | Bundet Boekfa Thana Maihom Masahiro Ehara Jumras Limtrakul Investigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculations Scientific Reports |
| title | Investigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculations |
| title_full | Investigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculations |
| title_fullStr | Investigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculations |
| title_full_unstemmed | Investigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculations |
| title_short | Investigation of the Suzuki–Miyaura cross-coupling reaction on a palladium H-beta zeolite with DFT calculations |
| title_sort | investigation of the suzuki miyaura cross coupling reaction on a palladium h beta zeolite with dft calculations |
| url | https://doi.org/10.1038/s41598-023-51116-x |
| work_keys_str_mv | AT bundetboekfa investigationofthesuzukimiyauracrosscouplingreactiononapalladiumhbetazeolitewithdftcalculations AT thanamaihom investigationofthesuzukimiyauracrosscouplingreactiononapalladiumhbetazeolitewithdftcalculations AT masahiroehara investigationofthesuzukimiyauracrosscouplingreactiononapalladiumhbetazeolitewithdftcalculations AT jumraslimtrakul investigationofthesuzukimiyauracrosscouplingreactiononapalladiumhbetazeolitewithdftcalculations |