Issue 25, 2018
From the journal:

Organic & Biomolecular Chemistry

Oxidation of α-trifluoromethyl and non-fluorinated alcohols via the merger of oxoammonium cations and photoredox catalysis†

Vincent A. Pistritto, ORCID logo a   Joshua M. Paolillo, ORCID logo a   Kathryn A. Bisset ORCID logo a  and  Nicholas E. Leadbeater ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269, USA
E-mail: nicholas.leadbeater@uconn.edu

Abstract

We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good yields. The methodology serves as an improvement over previous reports of an analogous oxidation strategy requiring superstoichiometric quantities of oxidant. Both primary and secondary non-fluorinated alcohols can also be oxidised in good yields.

Graphical abstract: Oxidation of α-trifluoromethyl and non-fluorinated alcohols via the merger of oxoammonium cations and photoredox catalysis

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Article information

DOI
https://doi.org/10.1039/C8OB01063C
Article type
Paper
Submitted
07 May 2018
Accepted
05 Jun 2018
First published
05 Jun 2018

Org. Biomol. Chem., 2018,16, 4715-4719

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Oxidation of α-trifluoromethyl and non-fluorinated alcohols via the merger of oxoammonium cations and photoredox catalysis

V. A. Pistritto, J. M. Paolillo, K. A. Bisset and N. E. Leadbeater, Org. Biomol. Chem., 2018, 16, 4715 DOI: 10.1039/C8OB01063C

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