Concepedia

Oxidation of Alkyl Trifluoroborates: An Opportunity for Tin‐Free Radical Chemistry

Geoffroy Sorin, Rocio Martinez Mallorquin, Yohan Contie, Alexandre Baralle, Max Malacrìa, Jean‐Philippe Goddard, Louis Fensterbank

Angewandte Chemie · 2010 · 45 citations · 38 references

DOI

Concepts

Abstract

Abfangexperimente mit TEMPO belegen, dass Organotrifluoroborate durch Kupfer(II)-Salze und Dess-Martin-Periodinan über radikalische Intermediate oxidiert werden. Auf diesem Weg erzeugte Radikale ermöglichen Funktionalisierungen und C-C-Kupplungen durch Giese-Additionen (siehe Schema; DMSO=Dimethylsulfoxid, TEMPO=2,2,6,6-Tetramethyl-1-piperidinyloxyl).

References

38

Efficient Visible Light Photocatalysis of [2+2] Enone Cycloadditions

Michael A. Ischay, Mary E. Anzovino, Juana Du et al. · Journal of the American Chemical Society · 2008 · 1.1K citations

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Electron-Transfer Photoredox Catalysis: Development of a Tin-Free Reductive Dehalogenation Reaction

Jagan M. R. Narayanam, Joseph W. Tucker, Corey R. J. Stephenson · Journal of the American Chemical Society · 2009 · 976 citations

, , +16

Organotrifluoroborates:  Protected Boronic Acids That Expand the Versatility of the Suzuki Coupling Reaction

Gary A. Molander, Noel M. Ellis · Accounts of Chemical Research · 2007 · 923 citations

, , +14

Direct C−H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids

Ian B. Seiple, Shun Su, Rodrigo A. Rodriguez et al. · Journal of the American Chemical Society · 2010 · 591 citations

, , +14

Rate constants and Arrhenius parameters for the reactions of primary, secondary, and tertiary alkyl radicals with tri-n-butyltin hydride

Chryssostomos Chatgilialoglu, K. U. Ingold, J. C. Scaiano · Journal of the American Chemical Society · 1981 · 341 citations

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