Just Published in Chemistry - A European Journal

Authors: Udo Radius, Ursula S. D. Paul

Abstract: Herein we report our studies, initially on C-F bond activation by cAAC-stabilized nickel(0) complex [Ni(cAACmethyl)2] (2), which then led to observation of C-F bond cleavage of perfluorinatied arenes by the carbene ligand cAACmethyl (1) itself. We were able to investigate further transformations of the obtained activation products (cAACmethyl)F(Arf) 4a-d in fluoride abstraction or fluorine transfer reactions. To get an insight into the chemoselectivity of these reactions, we treated carbine 1 with partially fluorinated arenes, which led to the observation of C-H bond activation. To evaluate the basicity of cAACmethyl (1) in more detail and to compare it with the results obtained for the related NHCs, we also performed reactions towards common C-H acidic reagents, such as imidazolium salts, imidazoles, esters and even trimethylphosphine.

Link: http://onlinelibrary.wiley.com/doi/10.1002/chem.201605950/abstract