Bis(trifluoromethanesulfonyl)imide

Introduction

Bis(trifluoromethanesulfonyl)imide (1), or triflimide, is a commercially available Brønsted acid that has been applied to a broad range of organic transformations. [¹] In addition to being an exceptionally potent Brønsted acid, the corresponding conjugate base is more commonly employed as a weakly coordinating counterion with a variety of metal and organic catalyst systems. [²] Experimental evidence indicates that triflimide is a weaker Brønsted acid in solution than the closely related triflic acid, [³] however, the lower charge density and greater steric encumbrance ­results in a less coordinating anion. Consequently, tri­flimide-based Lewis acids generally show higher activity than their corresponding triflate counterparts. [4]

References

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1

J. Sun, Triflimide, In e-EROS Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, 2010; http://onlinelibrary.wiley.com/o/eros/articles/rn01222/frame.html