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RSC Advances
probably converted to normal 7 again (Fig. S3†). Thus, reac-
tivation with AgOTf was carried out. The resuscitated 7A
demonstrated the same level of activity as that of fresh 7A, giving
product 13a within 3 h (21st–23rd runs). Clearly, the catalyst was
available for further reaction.
Green Chem., 2015, 17, 4178; (f) K. L. Luska, J. Julis,
E. Stavitski, D. N. Zakharov, A. Adams and W. Leitner,
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Conclusions
In summary, we have developed a novel mercury salt polymer
catalyst stabilized by m-carbaborane which has been applied to
the regioselective synthesis of allyl- and vinyl-substituted cyclic
compounds and allyl amine derivatives from a wide range of
1,3-dienes and allyl alcohols. The catalyst precursor 7 can be
easily prepared in a one-pot process from m-carbaborane, and it
has high durability under acidic conditions. Catalyst 7A can be
recovered without mercury leakage, and revitalization is
possible by simple treatment with aqueous HCl and AgOTf
when catalytic activity decreases through repeated use. To the
best of our knowledge, the present catalyst is the rst utilizing
m-carbaborane to safely concatenate a heavy metal and a poly-
mer material. It has distinctive reactivity (towards 1,3-dienes),
and its reactivity constitutes a reasonable alternative to existing
mercury salt reagents. We rmly believe that it will be proved
quite useful in organic syntheses from utility, safety and green
chemistry perspectives.
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Acknowledgements
Dedicated to the late Professor Mugio Nishizawa. We are
grateful to Dr Yasuko Okamoto (analysis center in Tokushima
Bunri University) for determining the HRMS. This study was
nancially supported by a Grant-in-Aid (No. 23790034) from the
MEXT (Ministry of Education, Culture, Sports, Science, and
Technology) of the Japanese Government.
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