Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate
Site-selective functionalization of pyridines is a crucial tool for the synthesis of diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient and potent Lewis acids. We report that tributylphosphine selectively adds to the 4-position of pyridine in tetrame...
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MDPI AG
2023-08-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/3/M1710 |
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| author | Yiwei Gong Jas S. Ward Kari Rissanen Florian F. Mulks |
| author_facet | Yiwei Gong Jas S. Ward Kari Rissanen Florian F. Mulks |
| author_sort | Yiwei Gong |
| collection | DOAJ |
| description | Site-selective functionalization of pyridines is a crucial tool for the synthesis of diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient and potent Lewis acids. We report that tributylphosphine selectively adds to the 4-position of pyridine in tetramethyldiiminium pyridine ditrifluoromethanesulfonate, resulting in the formation of the title compound. This finding represents an advancement towards the utilization of diiminium units as organic reagents or catalysts for pyridine functionalization. We also employ computational models to determine fluoride and hydride ion affinities, Fukui function <i>f</i><sup>+</sup>(r), molecular electrostatic potential, and p<i>K</i>a values, providing valuable insights for future investigations in this area. |
| first_indexed | 2024-03-10T22:26:01Z |
| format | Article |
| id | doaj.art-5b5615a6d2c6415b896605537dfd3fd9 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T22:26:01Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-5b5615a6d2c6415b896605537dfd3fd92023-11-19T12:06:59ZengMDPI AGMolbank1422-85992023-08-0120233M171010.3390/M1710Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium DitrifluoromethanesulfonateYiwei Gong0Jas S. Ward1Kari Rissanen2Florian F. Mulks3Institute for Organic Chemistry (IOC), RWTH Aachen University, Landoltweg 1, 52074 Aachen, GermanyDepartment of Chemistry, University of Jyvaskyla, P.O. Box 35, 40014 Jyväskylä, FinlandDepartment of Chemistry, University of Jyvaskyla, P.O. Box 35, 40014 Jyväskylä, FinlandInstitute for Organic Chemistry (IOC), RWTH Aachen University, Landoltweg 1, 52074 Aachen, GermanySite-selective functionalization of pyridines is a crucial tool for the synthesis of diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient and potent Lewis acids. We report that tributylphosphine selectively adds to the 4-position of pyridine in tetramethyldiiminium pyridine ditrifluoromethanesulfonate, resulting in the formation of the title compound. This finding represents an advancement towards the utilization of diiminium units as organic reagents or catalysts for pyridine functionalization. We also employ computational models to determine fluoride and hydride ion affinities, Fukui function <i>f</i><sup>+</sup>(r), molecular electrostatic potential, and p<i>K</i>a values, providing valuable insights for future investigations in this area.https://www.mdpi.com/1422-8599/2023/3/M1710pyridine functionalizationdihydropyridineLewis acidsorganic Lewis acidsdicationsdiiminium |
| spellingShingle | Yiwei Gong Jas S. Ward Kari Rissanen Florian F. Mulks Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate Molbank pyridine functionalization dihydropyridine Lewis acids organic Lewis acids dications diiminium |
| title | Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate |
| title_full | Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate |
| title_fullStr | Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate |
| title_full_unstemmed | Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate |
| title_short | Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate |
| title_sort | tributyl 1 dimethylamino dimethyliminio methyl 1 4 dihydropyridin 4 yl phosphonium ditrifluoromethanesulfonate |
| topic | pyridine functionalization dihydropyridine Lewis acids organic Lewis acids dications diiminium |
| url | https://www.mdpi.com/1422-8599/2023/3/M1710 |
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