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Issue 8, 2014
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Visible-light-induced photocatalytic formyloxylation reactions of 3-bromooxindoles with water and DMF: the scope and mechanism

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Abstract

The formyloxylation reaction of 3-bromooxindoles with water and N,N-dimethylformamide (DMF) has been developed in the presence of the photoredox catalyst fac-Ir(ppy)3 under irradiation of visible light at ambient temperature. The reaction provides a straightforward approach to pharmaceutically and synthetically useful 3-formyloxyoxindoles in high yields. The mechanism of this transformation was investigated by fluorescence quenching experiments, “on–off” switching of the light source, labeling experiments, mass spectral analyses and in situ IR experiments.

Graphical abstract: Visible-light-induced photocatalytic formyloxylation reactions of 3-bromooxindoles with water and DMF: the scope and mechanism

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Supplementary files

Article information


Submitted
10 Apr 2014
Accepted
08 May 2014
First published
08 May 2014

Green Chem., 2014,16, 3787-3795
Article type
Paper
Author version available

Visible-light-induced photocatalytic formyloxylation reactions of 3-bromooxindoles with water and DMF: the scope and mechanism

Y. Zou, W. Guo, F. Liu, L. Lu, J. Chen and W. Xiao, Green Chem., 2014, 16, 3787
DOI: 10.1039/C4GC00647J

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