Issue 27, 2016
From the journal:

Organic & Biomolecular Chemistry

Efficient generation of perfluoroalkyl radicals from sodium perfluoroalkanesulfinates and a hypervalent iodine(iii) reagent: mild, metal-free synthesis of perfluoroalkylated organic molecules†

Ryu Sakamoto,a   Hirotaka Kashiwagi,a   Sermadurai Selvakumar,a   Shin A. Motekia  and  Keiji Maruoka*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
E-mail: maruoka@kuchem.kyoto-u.ac.jp
Fax: +81-75-753-4041
Tel: +81-75-753-4041

Abstract

This article describes an efficient method for the introduction of perfluoroalkyl groups into N-acrylamides, 2-isocyanides, olefins, and other heterocycles using perfluoroalkyl radicals that were generated from the reaction between sodium perfluoroalkanesulfinates and a hypervalent iodine(III) reagent. This approach represents a simple, scalable perfluoroalkylation method under mild and metal-free conditions.

Graphical abstract: Efficient generation of perfluoroalkyl radicals from sodium perfluoroalkanesulfinates and a hypervalent iodine(iii) reagent: mild, metal-free synthesis of perfluoroalkylated organic molecules

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Article information

DOI
https://doi.org/10.1039/C6OB01245K
Article type
Communication
Submitted
08 Jun 2016
Accepted
09 Jun 2016
First published
09 Jun 2016

Org. Biomol. Chem., 2016,14, 6417-6421

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Efficient generation of perfluoroalkyl radicals from sodium perfluoroalkanesulfinates and a hypervalent iodine(III) reagent: mild, metal-free synthesis of perfluoroalkylated organic molecules

R. Sakamoto, H. Kashiwagi, S. Selvakumar, S. A. Moteki and K. Maruoka, Org. Biomol. Chem., 2016, 14, 6417 DOI: 10.1039/C6OB01245K

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