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Mechanistic insight into the thermal activation of Togni's trifluoromethylation reagents

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Abstract

Herein we investigate the propensity of hypervalent iodine based electrophilic trifluoromethylating agents to undergo thermally induced fragmentation of the F3C–I–O motif. For the first time we are able to observe a dissociative electron transfer mechanism using mass spectroscopy techniques to generate and trap CF3 radicals. Consistent with this mechanism, alkyl radical elimination from these reagents is in full support of an intermediate cyclic iodanyl radical and a reagent-specific temperature of maximum radical production was found to correlate with reported solution phase reactivity.

Graphical abstract: Mechanistic insight into the thermal activation of Togni's trifluoromethylation reagents

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Publication details

The article was received on 03 Mar 2017, accepted on 21 May 2017 and first published on 25 May 2017


Article type: Communication
DOI: 10.1039/C7CP01396E
Citation: Phys. Chem. Chem. Phys., 2017, Advance Article
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    Mechanistic insight into the thermal activation of Togni's trifluoromethylation reagents

    N. Santschi, B. J. Jelier and T. Nauser, Phys. Chem. Chem. Phys., 2017, Advance Article , DOI: 10.1039/C7CP01396E

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