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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1539-1551
Published online, 26th September, 2013
DOI: 10.3987/COM-13-S(S)80
■ Facile Formation of Imidazolinium Salt by Reaction of Corresponding Diamine and Trimethyl Orthoformate in 1,1,1,3,3,3-Hexafluoroisopropanol

Kensuke Usui and Masahisa Nakada*

*Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

The preparation of imidazolinium salts, which can be used as precursors of pincer-type N-heterocyclic carbene ligands, is described. The formation of imidazolinium salts under standard conditions is difficult, but they have been successfully synthesized by reaction of the corresponding diamines and trimethyl orthoformate in 1,1,1,3,3,3-hexafluoroisopropanol. The synthesis of new chiral C2 symmetric imidazolinium salts is also described.