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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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Publication details

The article was received on 16 Mar 2018, accepted on 28 Apr 2018 and first published on 30 Apr 2018


Article type: Edge Article
DOI: 10.1039/C8SC01249K
Citation: Chem. Sci., 2018,9, 5354-5359
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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

    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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