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


Publication year2023

Publication date09/08/2023


Issue number3

Article numberM1710

PublisherMDPI AG

Publication countrySwitzerland

Publication languageEnglish


Publication open accessOpenly available

Publication channel open accessOpen Access channel

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


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