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Issue 67, 2018
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Intriguing migrations in transient iminoborane adducts: two new pathways to aminoboranes

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Abstract

Two unusual reactions were demonstrated with iminoboranes, both leading to aminoboranes of the type R2B[double bond, length as m-dash]NR2. In one case, a carboboration of di(tert-butyl)iminoborane with B(C6F5)3 led to (tBu)(C6F5)B–N(tBu)(B(C6F5)2). In the other, a transient IDipp (1,3-di(2,6-diisopropylphenyl)imidazol-2-ylidene) adduct of MesBNtBu undergoes a shift of one carbene-bound Dipp substituent to the iminoborane nitrogen atom, yielding (1-Dipp-imidazol-2-yl)(Mes)B–N(Dipp)(tBu). Mechanistic DFT studies indicate the intermediacy of a borane·iminoborane adduct in the carboboration reaction.

Graphical abstract: Intriguing migrations in transient iminoborane adducts: two new pathways to aminoboranes

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Article information


Submitted
29 Jun 2018
Accepted
25 Jul 2018
First published
26 Jul 2018

Chem. Commun., 2018,54, 9349-9351
Article type
Communication

Intriguing migrations in transient iminoborane adducts: two new pathways to aminoboranes

L. Winner, G. Bélanger-Chabot, M. A. Celik, M. Schäfer and H. Braunschweig, Chem. Commun., 2018, 54, 9349
DOI: 10.1039/C8CC05220D

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