An Efficient Synthesis of Imidazolinium Salts Using Vinyl Sulfonium Salts
Eoghan M. McGarrigle*, Sven P. Fritz, Ludovic Favereau, Muhammad Yar and Varinder K. Aggarwal*
*School of Chemistry, University of Bristol, Cantock's Close,
Bristol BS8 1TS, U.K., Email: eoghan.mcgarrigle
bristol.ac.uk,
V.Aggarwalbristol.ac.uk
E. M. McGarrigle, S. P. Fritz, L. Favereau, M. Yar, V. K. Aggarwal, Org. Lett., 2011, 13, 3060-3063.
DOI: 10.1021/ol2009472
Abstract
The reaction of formamidines and (2-bromoethyl)diphenylsulfonium triflate enables the synthesis of various symmetrical and unsymmetrical imidazolinium triflate salts in high yield in short reaction times under mild conditions. Aromatic and aliphatic N-substituents work well. The reaction is proposed to proceed via generation of a vinyl sulfonium salt intermediate from the bromoethylsulfonium triflate.
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ID: J54-Y2011-1690
