Lovera, Sergio O. and Bagsdasarian, Alex L. and Guo, Juchen and Nelson, Hosea M. and Lavallo, Vincent (2022) Cesium carbonate mediated C–H functionalization of perhalogenated 12-vertex carborane anions. Chemical Communications, 58 (25). pp. 4060-4062. ISSN 1359-7345. doi:10.1039/d2cc00173j. https://resolver.caltech.edu/CaltechAUTHORS:20220309-982495000
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Abstract
C–H functionalization of undecahalogenated carborane anions, [HCB₁₁X₁₁⁻] (X = Cl, Br, I), is performed with Cs₂CO₃ in acetonitrile. We show that the requisite Cl, Br and I carborane dianions can all be efficiently accessed with Cs₂CO₃. The utilization of Cs₂CO₃ eliminates the complications associated with competing E2 elimination reactions providing an efficient, more functional group tolerant, and broader scope than previously reported. The ensuing functionalized cages provide potential synthons for constructing advanced materials and other molecular architectures for various applications.
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| Additional Information: | © The Royal Society of Chemistry 2022. Submitted 10 Jan 2022. Accepted 03 Mar 2022. First published 07 Mar 2022. This article is part of the themed collection: Boron Chemistry in the 21st Century: From Synthetic Curiosities to Functional Molecules. All authors contributed equally to the manuscript. V. L. and J. G. gratefully thank the National Science Foundation (DMR-2004497) for supporting this investigation. H. M. N. thanks the N. I. H.-NIGMS for funding (R35-GM128936). There are no conflicts to declare. | |||||||||||||||
| Errata: | Correction: Cesium carbonate mediated C–H functionalization of perhalogenated 12-vertex carborane anions. Chem. Commun., 2022, 58, 6558-6558; DOI: 10.1039/d2cc90180c | |||||||||||||||
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| Issue or Number: | 25 | |||||||||||||||
| DOI: | 10.1039/d2cc00173j | |||||||||||||||
| Record Number: | CaltechAUTHORS:20220309-982495000 | |||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20220309-982495000 | |||||||||||||||
| Official Citation: | Cesium carbonate mediated C–H functionalization of perhalogenated 12-vertex carborane anions. Chem. Commun., 2022, 58, 4060-4062; DOI: 10.1039/d2cc00173j | |||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||||||||
| ID Code: | 113817 | |||||||||||||||
| Collection: | CaltechAUTHORS | |||||||||||||||
| Deposited By: | George Porter | |||||||||||||||
| Deposited On: | 09 Mar 2022 23:01 | |||||||||||||||
| Last Modified: | 29 Jun 2022 00:06 |
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