Fe⊕-Induced Dehydrogenation of 2-Octyne in the Gas Phase – Evidence for Direct Functionalization of Remote C-H Bonds

Abstract

Experimental evidence is presented that the Fe^⊕-induced dehydrogenation of gaseous 2-octyne cannot be described in terms of the traditional reaction sequence, i.e. oxidative addition of Fe^⊕ to a carbon-carbon bond followed by β-hydrogen transfers to the metal centre. Rather, the major reaction path commences with direct insertion of the complexed Fe^⊕ into a remote C–H bond. The so-formed iron-metallacycle serves as central intermediate for the regiospecific losses of both hydrogen and ethylene.