Cargando…
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...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3628290/ https://www.ncbi.nlm.nih.gov/pubmed/23616815 http://dx.doi.org/10.3762/bjoc.9.79 |
_version_ | 1782266406901907456 |
---|---|
author | Shaik, Jeelani Basha Ramkumar, Venkatachalam Varghese, Babu Sankararaman, Sethuraman |
author_facet | Shaik, Jeelani Basha Ramkumar, Venkatachalam Varghese, Babu Sankararaman, Sethuraman |
author_sort | Shaik, Jeelani Basha |
collection | PubMed |
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. |
format | Online Article Text |
id | pubmed-3628290 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-36282902013-04-24 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 Shaik, Jeelani Basha Ramkumar, Venkatachalam Varghese, Babu Sankararaman, Sethuraman Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2013-04-10 /pmc/articles/PMC3628290/ /pubmed/23616815 http://dx.doi.org/10.3762/bjoc.9.79 Text en Copyright © 2013, Shaik et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Shaik, Jeelani Basha Ramkumar, Venkatachalam Varghese, Babu Sankararaman, Sethuraman 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 | 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 | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3628290/ https://www.ncbi.nlm.nih.gov/pubmed/23616815 http://dx.doi.org/10.3762/bjoc.9.79 |
work_keys_str_mv | AT shaikjeelanibasha synthesisandstructureoftransbis14dimesityl3methyl123triazol5ylidenepalladiumiidichlorideanddiacetatesuzukimiyauracouplingofpolybromoareneswithhighcatalyticturnoverefficiencies AT ramkumarvenkatachalam synthesisandstructureoftransbis14dimesityl3methyl123triazol5ylidenepalladiumiidichlorideanddiacetatesuzukimiyauracouplingofpolybromoareneswithhighcatalyticturnoverefficiencies AT varghesebabu synthesisandstructureoftransbis14dimesityl3methyl123triazol5ylidenepalladiumiidichlorideanddiacetatesuzukimiyauracouplingofpolybromoareneswithhighcatalyticturnoverefficiencies AT sankararamansethuraman synthesisandstructureoftransbis14dimesityl3methyl123triazol5ylidenepalladiumiidichlorideanddiacetatesuzukimiyauracouplingofpolybromoareneswithhighcatalyticturnoverefficiencies |