A simple access to metallic or onium bistrifluoromethanesulfonimide salts

Numerous salts of the (CF3SO2)2N− anion, called TFSI, were prepared according to an original one-pot procedure. First, N-benzyl trifluoromethanesulfonimide (N-benzyl triflimide) was treated with ethanol to form an oxonium intermediate, which was then neutralized by various bases to provide metallic...

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Bibliographic Details
Published in:Tetrahedron 2009-07, Vol.65 (27), p.5361-5368
Main Authors: Arvai, Roman, Toulgoat, Fabien, Langlois, Bernard R., Sanchez, Jean-Yves, Médebielle, Maurice
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:Numerous salts of the (CF3SO2)2N− anion, called TFSI, were prepared according to an original one-pot procedure. First, N-benzyl trifluoromethanesulfonimide (N-benzyl triflimide) was treated with ethanol to form an oxonium intermediate, which was then neutralized by various bases to provide metallic or trialkylammonium triflimides salts. Alternatively, N-benzyl triflimide was directly treated with trialkyl sulfonium, quaternary ammonium or phosphonium halides to deliver the corresponding triflimide derivatives. N-Benzyl triflimide can be also reacted with di- or tri-alkylamines and phosphines to get benzyl onium salts. Analogous reactions can be carried out with N-allyl triflimide. Therefore, the TFSI anion can be very easily and expediently associated with a wide range of metallic or organic cations. Such salts can find applications as electrolytes for batteries and fuel cells, ionic liquids or Lewis acids. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.04.068