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Communication
Further studies on the applications of this strategy will be
reported in due course.
Acknowledgements
Scheme 3 Labeling experiments.
We are grateful for nancial support from the National Natural
Science Foundation of China (Grant 21032001, 21272085).
Notes and references
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Scheme 4 A plausible mechanism.
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Fig. 2 X-ray crystal structure of compound C.
´
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determined by X-ray crystallographic analysis (Fig. 1).14
To gain some insight into the mechanism of the reaction, an
O18-labeled H2O experiment with 1a using TBHP dissolution in
decane was performed, and obvious detection of 18O–2aa by
mass analysis suggested that the oxygen of hydroxy of 2a orig-
inated from H2O (Scheme 3).
According to the aforementioned information, we suggest a
possible reaction mechanism which is depicted in Scheme 4.
Initially, the iodine molecule promoted the transformation of 1-
bromo-4-vinylbenzene 1g into the iodonium intermediate A,
which was subsequently attacked by water to provide the
intermediate B. Fortunately, we separated the by-product C
which can give another abundant proof that intermediate A was
attacked by water. Moreover, compound C was further deter-
mined by X-ray crystallographic analysis (Fig. 2).15 However, C
could not be oxidized into nal product 2g. Therefore, it is
suggested that intermediate B was selectively oxidized to form
the target product 2g.
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In conclusion, a new method has been developed for the I2-
promoted activation and oxidation of olens. The protocol
provides an efficient, green and readily accessible method to
synthesize a-hydroxyacetophenones through oxidative 1,2-
difunctionalization of styrenes under milder conditions.16
51182 | RSC Adv., 2014, 4, 51180–51183
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