Iron carbene complexes have been implicated as key organometallic intermediates in valuable synthetic transformations, such as olefin cyclopropanation and C-H alkylation. Although widely considered to be operative in these reactions, iron carbenes have often precluded isolation and direct study. Consequently, a limited number of isolable iron carbene complexes have been reported in the literature to date. Herein, we describe the preparation of an unusual paramagnetic pyridine dipyrrolide iron carbene complex, (MesPDPPh)Fe(CPh2), which has been characterized via 1H NMR, Mössbauer, SQUID magnetometry, and X-ray crystallography. A complimentary full-molecule density functional theory study has been conducted to further probe the electronic structure of this complex, which is best described as possessing a monoanionic radical carbene ligand. Initial reactivity studies of (MesPDPPh)Fe(CPh2) with carbon monoxide and isocyanides revealed rich insertion and group transfer chemistries, a summary of which will be presented.

Synthesis, electronic structure, and reactivity of a pyridine dipyrrolide iron carbene

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.