A1 Journal article (refereed)
Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate (2023)


Gong, Y., Ward, J. S., Rissanen, K., & Mulks, F. F. (2023). Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate. Molbank, 2023(3), Article M1710. https://doi.org/10.3390/m1710


JYU authors or editors


Publication details

All authors or editorsGong, Yiwei; Ward, Jas S.; Rissanen, Kari; Mulks, Florian F.

Journal or seriesMolbank

eISSN1422-8599

Publication year2023

Publication date09/08/2023

Volume2023

Issue number3

Article numberM1710

PublisherMDPI AG

Publication countrySwitzerland

Publication languageEnglish

DOIhttps://doi.org/10.3390/m1710

Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/88836


Abstract

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 f + (r), molecular electrostatic potential, and pKa values, providing valuable insights for future investigations in this area.


Keywordsorganic chemistrychemical synthesisorganic compoundscations

Free keywordspyridine functionalization; dihydropyridine; Lewis acids; organic Lewis acids; dications; diiminium; cations


Contributing organizations


Ministry reportingYes

Reporting Year2023

JUFO rating0


Last updated on 2024-03-07 at 00:06