Issue 6, 2015

Generation of 1,2-azaboretidines via reduction of ADC borane adducts

Abstract

Reaction of the acyclic (diamino)carbene (ADC) :C(NiPr2)2 (1) with different dihaloboranes of the type RBX2 (R = Mes, Dur; X = Cl, Br) smoothly afforded a novel class of ADC-stabilized borane adducts. For MesBBr2 however, the reaction did not stop at the adduct level, but an uncommon rearrangement process occurred, which eventually resulted in the formation of a 5-membered boracycle after elimination of mesitylene. Chemical reduction of the ADC borane adducts by KC8 selectively yielded air stable 1,2-azaboretidines. Detailed DFT studies suggest a reduction mechanism involving a highly reactive borylene intermediate, which is converted into the boracycles via a rearrangement/C–H activation sequence.

Graphical abstract: Generation of 1,2-azaboretidines via reduction of ADC borane adducts

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Mar 2015
Accepted
16 Apr 2015
First published
16 Apr 2015
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., 2015,6, 3461-3465

Generation of 1,2-azaboretidines via reduction of ADC borane adducts

H. Braunschweig, A. Gackstatter, T. Kupfer, T. Scheller, F. Hupp, A. Damme, N. Arnold and W. C. Ewing, Chem. Sci., 2015, 6, 3461 DOI: 10.1039/C5SC01077B

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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