Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies
trans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple Suzuki–Miyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and wi...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.9.79 |
| _version_ | 1831538970306019328 |
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| author | Jeelani Basha Shaik Venkatachalam Ramkumar Babu Varghese Sethuraman Sankararaman |
| author_facet | Jeelani Basha Shaik Venkatachalam Ramkumar Babu Varghese Sethuraman Sankararaman |
| author_sort | Jeelani Basha Shaik |
| collection | DOAJ |
| description | trans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple Suzuki–Miyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and with high turnover numbers. With 1,4-dibromobenzene the catalyst was found to be active for up to 13 consecutive cycles with a turnover number of 1260. The polyarylarenes were obtained in pure form after crystallization once without recourse to chromatographic purification. The single-crystal X-ray structures of the chloro (1) as well as the corresponding acetato (2) complexes are also reported and compared with the corresponding complexes of 1,4-diphenyl-3-methyl-1,2,3-triazol-5-ylidene as the ligand. |
| first_indexed | 2024-12-16T23:33:30Z |
| format | Article |
| id | doaj.art-6a205256f0f7498ea636f652e7ec56ff |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T23:33:30Z |
| publishDate | 2013-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-6a205256f0f7498ea636f652e7ec56ff2022-12-21T22:11:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-04-019169870410.3762/bjoc.9.791860-5397-9-79Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficienciesJeelani Basha Shaik0Venkatachalam Ramkumar1Babu Varghese2Sethuraman Sankararaman3Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, IndiaDepartment of Chemistry, Indian Institute of Technology Madras, Chennai 600036, IndiaSophisticated Analytical Instrument Facility, Indian Institute of Technology Madras, Chennai 600036, IndiaDepartment of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Indiatrans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple Suzuki–Miyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and with high turnover numbers. With 1,4-dibromobenzene the catalyst was found to be active for up to 13 consecutive cycles with a turnover number of 1260. The polyarylarenes were obtained in pure form after crystallization once without recourse to chromatographic purification. The single-crystal X-ray structures of the chloro (1) as well as the corresponding acetato (2) complexes are also reported and compared with the corresponding complexes of 1,4-diphenyl-3-methyl-1,2,3-triazol-5-ylidene as the ligand.https://doi.org/10.3762/bjoc.9.79C–C couplingN-heterocyclic carbenepalladiumSuzuki–Miyaura coupling1,2,3-triazolylidene |
| spellingShingle | Jeelani Basha Shaik Venkatachalam Ramkumar Babu Varghese Sethuraman Sankararaman Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies Beilstein Journal of Organic Chemistry C–C coupling N-heterocyclic carbene palladium Suzuki–Miyaura coupling 1,2,3-triazolylidene |
| title | Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies |
| title_full | Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies |
| title_fullStr | Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies |
| title_full_unstemmed | Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies |
| title_short | Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies |
| title_sort | synthesis and structure of trans bis 1 4 dimesityl 3 methyl 1 2 3 triazol 5 ylidene palladium ii dichloride and diacetate suzuki miyaura coupling of polybromoarenes with high catalytic turnover efficiencies |
| topic | C–C coupling N-heterocyclic carbene palladium Suzuki–Miyaura coupling 1,2,3-triazolylidene |
| url | https://doi.org/10.3762/bjoc.9.79 |
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