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Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes
Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C–H arylation. In the presence of a catalytic amount of Pd(OAc)(2), P(t-Bu(3))·HBF(4), and an excess of Cs(2)CO(3), the C–H arylation of TTF with several aryl br...
| Autores principales: | , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2020
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237811/ https://www.ncbi.nlm.nih.gov/pubmed/32509028 http://dx.doi.org/10.3762/bjoc.16.86 |
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| author | Yoshimura, Aya Kimura, Hitoshi Kagawa, Kohei Yoshioka, Mayuka Itou, Toshiki Vasu, Dhananjayan Shirahata, Takashi Yorimitsu, Hideki Misaki, Yohji |
| author_facet | Yoshimura, Aya Kimura, Hitoshi Kagawa, Kohei Yoshioka, Mayuka Itou, Toshiki Vasu, Dhananjayan Shirahata, Takashi Yorimitsu, Hideki Misaki, Yohji |
| author_sort | Yoshimura, Aya |
| collection | PubMed |
| description | Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C–H arylation. In the presence of a catalytic amount of Pd(OAc)(2), P(t-Bu(3))·HBF(4), and an excess of Cs(2)CO(3), the C–H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations. |
| format | Online Article Text |
| id | pubmed-7237811 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-72378112020-06-04 Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes Yoshimura, Aya Kimura, Hitoshi Kagawa, Kohei Yoshioka, Mayuka Itou, Toshiki Vasu, Dhananjayan Shirahata, Takashi Yorimitsu, Hideki Misaki, Yohji Beilstein J Org Chem Full Research Paper Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C–H arylation. In the presence of a catalytic amount of Pd(OAc)(2), P(t-Bu(3))·HBF(4), and an excess of Cs(2)CO(3), the C–H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations. Beilstein-Institut 2020-05-12 /pmc/articles/PMC7237811/ /pubmed/32509028 http://dx.doi.org/10.3762/bjoc.16.86 Text en Copyright © 2020, Yoshimura et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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 Yoshimura, Aya Kimura, Hitoshi Kagawa, Kohei Yoshioka, Mayuka Itou, Toshiki Vasu, Dhananjayan Shirahata, Takashi Yorimitsu, Hideki Misaki, Yohji Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes |
| title | Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes |
| title_full | Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes |
| title_fullStr | Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes |
| title_full_unstemmed | Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes |
| title_short | Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes |
| title_sort | synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237811/ https://www.ncbi.nlm.nih.gov/pubmed/32509028 http://dx.doi.org/10.3762/bjoc.16.86 |
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