C−F Bond Activation by a Saturated N‐Heterocyclic Carbene: Mesoionic Compound Formation and Adduct Formation with B(C6F5)3

Just a sip: Combination of the saturated N‐heterocyclic carbene 1,3‐bis(2,6‐diisopropylphenyl)‐imidazolin‐2‐ylidene (SIPr) and C₆F₆ led to a mesoionic compound, generated by C−F bond activation and deprotonation of the SIPr backbone. The reaction of the mesoionic compound with B(C₆F₅)₃ afforded an adduct where the fluoride atom from the C₆F₅ moiety coordinates to B(C₆F₅)₃.

Abstract

The reaction of SIPr, [1,3‐bis(2,6‐diisopropylphenyl)‐imidazolin‐2‐ylidene] (1), with C₆F₆ led to the formation of an unprecedented mesoionic compound (2). The formation of 2 is made accessible by deprotonation of the SIPr backbone with simultaneous elimination of HF. The C−F bond para to the imidazolium ring in 2 is only of 1.258(4) Å, which is the one of the shortest structurally authenticated C−F bonds known to date. The liberation of HF during the reaction is unequivocally proved by the addition of one more equivalent of SIPr, which leads to the imidazolium salt with the HF₂⁻ anion. To functionalize 2, the latter reacted with B(C₆F₅)₃ to give an unusual donor–acceptor compound, where the fluoride atom from the C₆F₅ moiety coordinates to B(C₆F₅)₃ and the carbanion moiety remains unaffected. Such coordination susceptibility of the fluoride atom of a nonmetallic system to a main‐group Lewis acid (F_non‐metal→BR₃) is quite unprecedented.

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