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. 2017 Nov 17;82(22):11703-11710.
doi: 10.1021/acs.joc.7b00934. Epub 2017 Jun 1.

Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides

Benjamin Janhsen  1 , Armido Studer  1
Affiliations

Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides

Benjamin Janhsen et al. J Org Chem. .

Abstract

Radical trifluoromethylation of aryl N,N-dimethyl hydrazones using TBAI as an initiator and Togni's reagent as a trifluoromethyl radical source is described. Cascades proceed via electron-catalysis; this approach is generally more applicable to hydrazone perfluoroalkylation using perfluoroalkyl iodides as the radical precursors in combination with a base under visible-light initiation.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Togni’s reagents I (1) and II (2).
Scheme 1
Scheme 1. Scope of the Trifluoromethylation
Scheme 2
Scheme 2. Postulated Mechanism for the Trifluoromethylation Using Togni Reagent
Scheme 3
Scheme 3. Scope of the Perfluoroalkylation
5 mol % of Bu6Sn2 was added.
Scheme 4
Scheme 4. Postulated Mechanism for the Hydrazone Perfluoroalkylation Using Perfluoroalkyl Iodides
See this image and copyright information in PMC

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