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Conclusions
In conclusion, we developed an efficient method for a
one-pot hydrogenation/oxygenation process to give access
to functionalized alkanes and phenol derivatives. Several
relatively inactive terminal and internal olefins with varying
substituents were hydrogenated in excellent yields, and aryl-
boronate compounds were simultaneously oxidized to sub-
stituted phenols with equal efficiency. The use of O2 as the
oxidant and the formation of the ultimately safe byproducts
N2 and B(OH)3 make the process environmentally attract-
ive. The practical utility of this method was further demon-
strated by performing a gram-scale experiment. Remarkable
rate acceleration of the aerobic diimide reduction of olefins
in the presence of a mild Lewis acidic arylboronate ester
is an attractive feature of this transformation. Hydrogen-
bonding activation of diimide was implicated in the reaction
pathway. Further studies toward expanding the scope of
this transformation with other classes of substrates are cur-
rently being pursued in our group.
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Supporting Information (see footnote on the first page of this arti-
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We gratefully acknowledge generous financial support from the Sci-
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