Organic & Biomolecular Chemistry
Paper
Y•−. Eosin Y•− has strong reduction potential and reduces O2 to
super O2 and regenerates the photocatalyst Eosin Y. On the
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•−
other hand, intermediate I was subsequently transformed to
•−
radical cation II which combined with O2 to afford peroxide
III. Finally the fragmentation of peroxide III gave the corres-
ponding aldehyde. The final fragmentation step was not very
clear at this stage since no useful intermediate was captured
using a GC-MS analysis of the reaction mixture.
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General procedure for the deprotection reaction
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1,3-Oxathiolane 1a (122 mg, 0.5 mmol) and Eosin Y (10 mg,
3 mol%) were added into MeCN (1.5 mL) in a 10 mL clear
Pyrex glass tube. The resulting mixture was stirred with a
Teflon-coated magnetic stir bar in air at room temperature for
3 h under visible-light irradiation generated from 6 W blue
LEDs. After completion of the reaction, the solvent was
removed under reduced pressure with a rotary evaporator and
the residue was purified by flash column chromatography on
silica gel to give the desired 4-bromobenzaldehyde (2a) as a
white solid (74 mg, 80%).
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Conclusions
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In summary, an efficient visible-light promoted aerobic de-
protection of 1,3-oxathiolanes was developed. Our method fea-
tured advantages such as mild conditions, good tolerance of
the functional group and easy performance which will expand
the application of the 1,3-oxathiolane protecting group in
organic synthesis.
Conflicts of interest
There are no conflicts to declare.
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Acknowledgements
We wish to acknowledge the generous financial support by the
NSFC (21472079) and the Fundamental Research Funds for
the Central Universities (xbmz–31920180053).
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Notes and references
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