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Issue 24, 2018
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Single and double activation of acetone by isolobal B[triple bond, length as m-dash]N and B[triple bond, length as m-dash]B triple bonds

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Abstract

B[triple bond, length as m-dash]N and B[triple bond, length as m-dash]B triple bonds induce C–H activation of acetone to yield a (2-propenyloxy)aminoborane and an unsymmetrical 1-(2-propenyloxy)-2-hydrodiborene, respectively. DFT calculations showed that, despite their stark electronic differences, both the B[triple bond, length as m-dash]N and B[triple bond, length as m-dash]B triple bonds activate acetone via a similar coordination-deprotonation mechanism. In contrast, the reaction of acetone with a cAAC-supported diboracumulene yielded a unique 1,2,3-oxadiborole, which according to DFT calculations also proceeds via an unsymmetrical diborene, followed by intramolecular hydride migration and a second C–H activation of the enolate ligand.

Graphical abstract: Single and double activation of acetone by isolobal B [[triple bond, length as m-dash]] N and B [[triple bond, length as m-dash]] B triple bonds

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Article information


Submitted
16 Mar 2018
Accepted
28 Apr 2018
First published
30 Apr 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 5354-5359
Article type
Edge Article

Single and double activation of acetone by isolobal B[triple bond, length as m-dash]N and B[triple bond, length as m-dash]B triple bonds

J. Böhnke, T. Brückner, A. Hermann, O. F. González-Belman, M. Arrowsmith, J. O. C. Jiménez-Halla and H. Braunschweig, Chem. Sci., 2018, 9, 5354
DOI: 10.1039/C8SC01249K

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