Synthesis of quaternary α-perfluoroalkyl lactams via electrophilic perfluoroalkylation

D Katayev; J Václavík; F Brüning; B Commare; A Togni

doi:10.1039/c6cc00700g

Synthesis of quaternary α-perfluoroalkyl lactams via electrophilic perfluoroalkylation

Chem Commun (Camb). 2016 Mar 14;52(21):4049-52. doi: 10.1039/c6cc00700g.

Authors

D Katayev¹, J Václavík², F Brüning¹, B Commare¹, A Togni¹

Affiliations

¹ Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, Vladimir-Prelog-Weg 2, 8093 Zürich, Switzerland. atogni@ethz.ch.
² Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, Vladimir-Prelog-Weg 2, 8093 Zürich, Switzerland. atogni@ethz.ch and Institute of Organic Chemistry and Biochemistry, v.v.i. Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague, Czech Republic.

PMID: 26893124
DOI: 10.1039/c6cc00700g

Abstract

Efficient protocols enabling the rapid installation of trifluoromethyl, as well as further functionalized fluoroalkyl groups by an electrophilic perfluoroalkylation of lactam-derived ketene silyl amides (KSAs) using hypervalent iodine reagents 1 and 2 have been developed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Ethylenes / chemistry
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry*
Indicators and Reagents / chemistry
Iodine / chemistry*
Ketones / chemistry
Lactams / chemical synthesis*
Lactams / chemistry
Molecular Structure

Substances

Ethylenes
Hydrocarbons, Fluorinated
Indicators and Reagents
Ketones
Lactams
Iodine
ketene