Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-)
1
Department of Chemistry, University of Colorado, Boulder, CO 80309-0215, USA
2
Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editors: Igor B. Sivaev, Narayan S. Hosmane and Bohumír Grűner
Molecules 2019, 24(20), 3779; https://doi.org/10.3390/molecules24203779
Received: 19 September 2019 / Revised: 9 October 2019 / Accepted: 9 October 2019 / Published: 21 October 2019
(This article belongs to the Special Issue Boron Chemistry and Its Development in the 21st Century: A Themed Issue Dedicated to Professor Bohumil Štíbr on the Occasion of His 80th Birthday)
We have examined the insertion of carbenes carrying leaving groups into the [nido-B11H13]2− dianion to form the [closo-1-CB11H12]− anion. The best procedure uses CF3SiMe3 and LiCl as the source of CF2. It is simple, convenient and scalable and proceeds with 70–90% yield. Density functional calculations have been used to develop a mechanistic proposal that accounts for the different behavior of CF2, requiring only one equivalent of base for successful conversion of Na[nido-B11H14]− to [closo-1-CB11H12]−, and CCl2 and CBr2, which require more.
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Keywords:
carboranes; [closo-1-CB11H12]− anion; difluorocarbene
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MDPI and ACS Style
Pecyna, J.; Rončević, I.; Michl, J. Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-). Molecules 2019, 24, 3779.
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