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Orga Pn l ie ca s&e Bd oi o nmo to al ed cj uu sl ta mr Ca rhg ei nms istry
DOI: 10.1039/C5OB01929J
Journal Name
ARTICLE
Scheme 4. A tentative mechanism
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Conclusions
In summary, we have uncovered
2
a
Bu
4
NI-catalyzed
chemoselective oxygenation of ketones to obtain a high α-
selectivity using TBHP as an oxidant. Reaction is
chemoselective, aryl methyl ketones, aliphatic ketones as well
as benzyllic position are inactive under the reaction condition.
The versatility of the reaction has been established by coupling
N-hydroxysuccinimide (NHSI), N-hydroxyphthilimde (NHPI), N-
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hydroxybenzotriazole
(HOBT)
and
1-hydroxy-7-
azabenzotriazole (HOAT) to a variety of ketones. The
application of teh reaction has been demonstrated by
synthesizing synthetically useful intermediates and products
vinyl phosphates as well as α-haloketone.
2
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Acknowledgements
The authors thank IISc, SERB (NO.SB/S1/OC-56/2013), New-
Delhi,and RL Fine Chem for financial support and Dr. A. R.
Ramesha (RL Fine Chem) for useful discussion. YS thanks CSIR
for a fellowship.
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