Issue 21, 2024

The borylamino-diborata-allyl anion

Abstract

Reactions of β-diketiminato alkaline earth alkyldiboranate derivatives [(BDI)Ae{pinBB(R)pin}] (BDI = HC{(Me)CNDipp}2; Dipp = 2,6-i-Pr2C6H3; Ae = Mg, R = n-Bu or Ae = Ca, R = n-hexyl) with t-BuNC provide access to the respective group 2 derivatives of unprecedented diborata-allyl, {(pinB)2CNBpin(t-Bu)}, anions. Although the necessary mode of B–C bond cleavage implicated in these transformations could not be elucidated, further studies of the reactivity of magnesium triboranates toward isonitriles delivered a more general and rational synthetic access to analogous anionic moieties. Extending this latter reactivity to a less symmetric triboranate variant also provided an isomeric Mg–C-bonded dibora-alkyl species and sufficient experimental insight to prompt theoretical evaluation of this reactivity. DFT calculations, thus, support a reaction pathway predicated on initial RNC attack at a peripheral boron centre and the intermediacy of such dibora-alkyl intermediates.

Graphical abstract: The borylamino-diborata-allyl anion

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Mar 2024
Accepted
28 Apr 2024
First published
30 Apr 2024
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., 2024,15, 7999-8007

The borylamino-diborata-allyl anion

H. T. W. Shere, H. Liu, S. E. Neale, M. S. Hill, M. F. Mahon and C. L. McMullin, Chem. Sci., 2024, 15, 7999 DOI: 10.1039/D4SC01953A

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