CaltechAUTHORS
  A Caltech Library Service

Cesium carbonate mediated C–H functionalization of perhalogenated 12-vertex carborane anions

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

[img] PDF - Supplemental Material
See Usage Policy.

4MB

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20220309-982495000

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/d2cc00173jDOIArticle
https://www.rsc.org/suppdata/d2/cc/d2cc00173j/d2cc00173j1.pdfPublisherSupplementary Information
https://doi.org/10.1039/d2cc90180cDOICorrection
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9157083/PubMed CentralCorrection
ORCID:
AuthorORCID
Bagsdasarian, Alex L.0000-0003-2281-8068
Guo, Juchen0000-0001-9829-1202
Nelson, Hosea M.0000-0002-4666-2793
Lavallo, Vincent0000-0001-8945-3038
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
Funders:
Funding AgencyGrant Number
NSFDMR-2004497
NIHR35 GM128936
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

Repository Staff Only: item control page