Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

How much fluoride is good for a strong electron‐withdrawing effect? In this review we summarize recent results on the use of perfluoroalkanesulfonates, 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.