Microwave-Assisted Iodination: Synthesis of Heavily Iodinated 10-Vertex and 12-Vertex Boron Clusters

References

• Reed, C. A. Carboranes: a new class of weakly coordinating anions for strong electrophiles, oxidants, and superacids. Acc. Chem. Res. 1998, 31, 133–139.
   Web of Science ®Google Scholar
• Douvris, C.; Michl, J. Update 1 of: Chemistry of the carba-closo-dodecaborate(−) anion, CB11H12−. Chem. Rev. 2013, 113, PR179–PR233.
   PubMed Web of Science ®Google Scholar
• Grüner, B.; Janoušek, Z.; King, B. T.; Woodford, J. N.; Wang, C. H.; Všetečka, V.; Michl, J. Synthesis of 12-substituted 1-carba-closo-dodecaborate anions and first hyperpolarizability of the 12-C7H6+-CB11H11− ylide. J. Am. Chem. Soc. 1999, 121, 3122–3126.
   Web of Science ®Google Scholar
• Himmelspach, A.; Finze, M. Ethynylmonocarba-closo-dodecaborates: M[12-HCC-closo-1-CB11H11] and M[7,12-(HCC)2-closo-1-CB11H10] (M = Cs+, [Et4N]+). J. Organomet. Chem. 2010, 695, 1337–1345.
   Web of Science ®Google Scholar
• Himmelspach, A.; Reiss, G. J.; Finze, M. Microwave-assisted Kumada-type cross-coupling reactions of iodinated carba-closo-dodecaborate anions. Inorg. Chem. 2012, 51, 2679–2688.
   PubMed Web of Science ®Google Scholar
• Rosenbaum, A. J.; Juers, D. H.; Juhasz, M. A. Copper-promoted cyanation of a boron cluster: synthesis, X-ray structure, and reactivity of 12-CN-closo-CHB11H10−. Inorg. Chem. 2013, 52, 10717–10719.
   PubMed Web of Science ®Google Scholar
• Zheng, Z.; Jiang, W.; Zinn, A. A.; Knobler, C. B.; Hawthorne, M. F. Facile electrophilic iodination of icosahedral carboranes. Synthesis of carborane derivatives with boron-carbon bonds via the palladium-catalyzed reaction of diiodocarboranes with Grignard reagents. Inorg. Chem. 1995, 34, 2095–2100.
   Web of Science ®Google Scholar
• Peymann, T.; Knobler, C.; Hawthorne, M. Synthesis of alkyl and aryl derivatives of closo-B12H122-- by the palladium-catalyzed coupling of closo-B12H11I2− with Grignard reagents. Inorg. Chem. 1998, 37, 1544–1548.
   Web of Science ®Google Scholar
• Srivastava, R. R.; Hamlin, D. K.; Wilbur, D. S. Synthesis of highly iodinated icosahedral mono- and dicarbon carboranes. J. Org. Chem. 1996, 61, 9041–9044.
   PubMed Web of Science ®Google Scholar
• Vaca, A.; Teixidor, F.; Kivekas, R.; Sillanpaa, R.; Vinas, C. A solvent-free regioselective iodination route of ortho-carboranes. Dalton Trans. 2006, 4884–4885.
   PubMed Web of Science ®Google Scholar
• Pepiol, A.; Teixidor, F.; Saralidze, K.; van der Marel, C.; Willems, P.; Voss, L.; Knetsch, M. L. W.; Vinas, C.; Koole, L. H. A highly radiopaque vertebroplasty cement using tetraiodinated o-carborane additive. Biomaterials 2011, 32, 6389–6398.
   PubMed Web of Science ®Google Scholar
• Franken, A.; Kilner, C.; Thornton-Pett, M.; Kennedy, J. Monocarbaborane anion chemistry. An interesting encapsulation of the Pd2I2{P(C6H4-4-Me3}4]2+ cation by a pair of [PhCB9H4I(C6H4Me]− anions. Chem. Commun. 2002, 2048–2049.
   PubMed Web of Science ®Google Scholar
• Xie, Z. W.; Manning, J.; Reed, R. W.; Mathur, R.; Boyd, P. D. W.; Benesi, A.; Reed, C. A. Approaching the silylium R3Si+ ion: Trends with hexahalo (Cl, Br, I) carboranes as counterions. J. Am. Chem. Soc. 1996, 118, 2922–2928.
   Web of Science ®Google Scholar
• Xie, Z.; Tsang, C.-W.; Sze, E. T.-P.; Yang, Q.; Chan, D. T. W.; Mak, T. C. W. Highly chlorinated, brominated, and iodinated icosahedral carborane anions: 1-H-CB11X11−, 1-CH3-CB11X11− (X = Cl, Br, I); 1-Br-CB11Br11−. Inorg. Chem. 1998, 37, 6444–6451.
   PubMed Web of Science ®Google Scholar
• Knoth, W. H.; Miller, H. C.; Sauer, J. C.; Balthis, J. H.; Chia, Y. T.; Muetterties, E. L. Chemistry of boranes. IX. Halogenation of B10H102− and B12H122−. Inorg. Chem. 1964, 3, 159–167.
   Web of Science ®Google Scholar
• Tsang, C.-W.; Yang, Q.; Sze, E. T.-P.; Mak, T. C. W.; Chan, D. T. W.; Xie, Z. Synthesis and structural characterization of highly chlorinated, brominated, iodinated, and methylated carborane anions, 1-H-CB9X9−, 1-NH2-CB9X9− (X = Cl, Br, I), and 1-H-CB9(CH3)9−. Inorg. Chem. 2000, 39, 3582–3589.
   PubMed Web of Science ®Google Scholar
• Valášek, M.; Štursa, J.; Pohl, R.; Michl, J. Microwave-assisted alkylation of CB11H12− and related anions. Inorg. Chem. 2010, 49, 10247–10254.
   PubMed Web of Science ®Google Scholar
• Plešek, J.; Jelínek, T.; Drdáková, E.; Heřmánek, S.; Štíbr, B. A convenient preparation of 1-CB11H12− and its C-amino derivatives. Collect. Czechoslov. Chem. Commun. 1984, 49, 1559–1562.
   Web of Science ®Google Scholar
• Ringstrand, B.; Bateman, D.; Shoemaker, R. K.; Janoušek, Z. Improved synthesis of closo-1-CB9H10− anion and new C-substituted derivatives. Collect. Czechoslov. Chem. Commun. 2009, 74, 419–431.
   Web of Science ®Google Scholar
• Hawthorne, M. F.; Pilling, R. L.; Knoth, W. H. Bis(triethylammonium) cecahydrodecaborate(2−). In Inorganic syntheses; Tyree, Jr., S. Y., Ed.; John Wiley & Sons, Inc., 2007; vol. 9, pp. 16–19.
   Google Scholar
• CrysAlis PRO; Agilent Technologies UK Ltd, Yarnton, England, 2011.
   Google Scholar
• Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341.
   Web of Science ®Google Scholar
• Jelínek, T.; Plešek, J.; Heřmánek, S.; Štíbr, B. Chemistry of compounds with the 1-carba-closo-dodecaborane(12) framework. Collect. Czechoslov. Chem. Commun. 1986, 51, 819–829.
   Web of Science ®Google Scholar