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Nine Times Fluoride Can Be Good For Your Syntheses. Not Just Cheaper: Nonafluorobutanesulfonates As Intermediates For Transition Metal-Catalyzed Reactions

Jens Hoegermeier, H. Reissig
Published 2009 · Chemistry

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How much fluoride is good for a strong electron-withdrawing effect? In this review we summarize recent results on the use of perfluoroalkane-sulfonates, in particular of the cost effective nonafluorobutanesulfonates (nonaflates), in transition metal-catalyzed reactions and a few other typical transformations. During the last decade many advantages over the commonly used triflates have been discovered. The generation of alkenyl and (het)aryl nonaflates and their applications in metal-catalyzed processes such as Heck, Suzuki, Sonogashira, Stille, and Negishi couplings or amination reactions are described. Although far from a systematic investigation, all the presented results clearly demonstrate the many advantages of nonaflates and of similar higher fluorinated sulfonates in laboratory and industrial scale organic synthesis. 1 Introduction 2 Alkyl Nonaflates 3 Alkenyl Nonaflates 4 Aryl and Hetaryl Nonaflates 5 Miscellaneous Reactions Including other Perfluorosulfonylated Reagents or Intermediates 6 Conclusion 7 Supplement Added in Proof.
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