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

Literature Information

Publication Date 2017-05-25
DOI 10.1039/C7CP01396E
Impact Factor 3.676
Authors

Nico Santschi, Benson J. Jelier, Thomas Nauser


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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.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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