Carborane Anions
My research interests center on the synthesis and computational studies
of molecules containing icosahedral boron clusters, especially
CB11H12-
and its derivatives.The derivatization chemistry of these compounds
is advancing, their applications are beginning to emerge,1,2
and there are a tremendous number of unexplored possibilities.

CB11H12- and some of its
derivatives.
Weakly
coordinating anions based on icosahedral carborane anions have been
used in the preparation of stable carbocations, 3,4 a
class of extremely strong solid Brønsted
acids,5,6 and a powerful new methylating reagent.7
Improved anion properties relative to those of the parent CB11H12-
anion have been achieved by attaching electron withdrawing and/or
bulky substituents around the exterior of the cage. For the most
part, efforts have focused on replacement of H-atom
substituents on the cage with either halogens,8 or with
alkyl9,10 and aryl8 groups and their
fluorinated analogues11. Tailoring properties of the
anion by modifying substituent patterns with other groups which may
confer improved weakly-coordinating properties has yet to be
explored. One major goal for this research is the preparation of new
derivatives of CB11H12- and the
evaluation of their performance as weakly-coordinating anions.
Advances
in the synthetic modifications which can be made to the CB11H12-
group can also be expected to improve its potential as a useful
moiety in Boron Neutron Capture Therapy, where the development
of CB11H12-
based systems has lagged that of the icosahedral
dicarbaboranes, (e.g. ortho-, meta-, and para-C2B10H12).
Grimes, Russel N., "Boron
Clusters Come of Age," Journal of Chemical Education,
2004, 5, 658-672.
Reed, C. A., "Carborane
Acids. New "Strong Yet Gentle'' Acids For Organic and
Inorganic Chemistry," Chemical Communications, 2005,
, 1669-1677.
Müller T., Juhasz, M.,
Reed, C. A., "The X-Ray Structure of a Vinyl Cation,"
Angewandte Chemie International Edition, 2004,
43, 1543-1546.
Kato, T., Reed, C. A., "Putting
t-Butyl Cation in a Bottle," Angewandte Chemie
International Edition, 2004, 43,
2908-2911.
Juhasz, M., Hoffmann, S.,
Stoyanov, E., Kim, K-C., Reed, C. A., "The Strongest Isolable
Acid," Angewandte Chemie International Edition, 2004,
40, 5352-5355.
Stoyanov, E. S., Hoffmann, S.
P., Juhasz, M., Reed, C. A., "The Structure of the Strongest
Brønsted Acid: The Carborane Acid H(CHB11Cl11),"
Journal of the American Chemical Society, 2006,
, 3160-3161.
Kato, T., Stoyanov, E., Geier,
J., Grutzmacher, H., Reed, C. A., "Alkylating Agents Stronger
than Alkyl Triflates," Journal of the American Chemical
Society, 2004, 126, 12451-12457.
Jelinek, T., Baldwin, P.,
Scheidt, W. R., Reed, C. A., "New Weakly Coordinating Anions.
2. Derivatization of the Carborane Anion CB11H12-," Inorganic
Chemistry, 1993, 32, 1982-1990.
King, B., Janousek, Z., Grüner,
B., Trammell, M., Noll, B. C., Michl, J.,
"Dodecamethylcarba-closo-dodecaborate(-) Anion, CB11Me12-,"
Journal of the American Chemical Society, 1996,
118, 3313-3314.
Stasko, D., Reed, C. A.,
"Optimizing the Least Nucleophilic Anion," Journal of
the American Chemical Society, 2002, 124,
1148-1149.
King, B. T., Michl, J., "The
Explosive "Inert" Anion CB11(CF3)12-," Journal
of the American Chemical Society, 2000,
122, 10255-10256.
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