Issue 24, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2018,9, 5354-5359

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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