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An unconventional cleavage of an unstrained carbon-carbon bond in allylic alcohols can be induced by the use of N -fluorobenzenesulfonimide (NFSI) under catalyst-free conditions. By using this simple procedure, a wide range of functionalized Z -fluoroalkenes can be accessed in high yield and selectivity from cyclic and acyclic allylic alcohols.

Divergent reactivities in fluoronation of allylic alcohols: synthesis of Z-fluoroalkenes via carbon–carbon bond cleavage