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Scheme 6. Proposed Reaction Mechanism
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a stepwise single-electron oxidation to achieve the carbocation
6 with the regeneration of the photocatalyst IrIII(ppy)3. Further
deprotonation of 6 offers the eventual product 3 in the
presence of base.
In conclusion, we have successfully developed an efficient
and practical strategy for the synthesis of fused benzo[e]-
isoindole-1,3,5-trione from α-bromo ketones and maleimides
via visible-light-induced reductive radical relay. This versatile
protocol proceeds through a cascade C(sp3)−Br/C(sp2)−H
functionalization, double C−C bond formation, and oxidative
aromatization sequence under mild conditions. Further activity
tests of these privileged structures are ongoing in our group.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
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Experimental details, characterization data of all
1
compounds, and copies of H and 13C NMR spectra
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Accession Codes
CCDC 1933382 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The authors acknowledge the National Innovation Experiment
Program for University Students (201910255071) and the
Fundamental Research Funds for the Central Universities and
Graduate Student Innovation Fund of Donghua University
(CUSF-DH-D-2018063 and BCZD2019004).
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