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Ring expansion of alumoles with organic azides: selective formation of six-membered aluminum–nitrogen heterocycles

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Abstract

Aside from simple Lewis acid–base chemistry, the reaction chemistry of aluminacyclopentadienes, which are commonly referred to as aluminoles or simply alumoles, remains relatively underdeveloped. To date, few attempts to extend their inherent insertion and cycloaddition reactivity to the construction of stable aluminum-containing heterocycles have been reported. Herein, we demonstrate the selective ring expansion of a cyclopentadienyl-substituted alumole with a series of organic azides to form unsaturated six-membered AlN heterocycles. Depending on the substituent on the azide, the reaction proceeds either with or without loss of dinitrogen, leading to incorporation of only the “NR” unit of the azide or the entire azo substituent into the periphery of the heterocycle. A deeper understanding of these ring expansion reactions is reached through computational studies, illustrating deviations in the mechanism as a function of the organic azide employed.

Graphical abstract: Ring expansion of alumoles with organic azides: selective formation of six-membered aluminum–nitrogen heterocycles

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Article information


Submitted
09 Apr 2020
Accepted
13 May 2020
First published
14 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Ring expansion of alumoles with organic azides: selective formation of six-membered aluminum–nitrogen heterocycles

R. Drescher, S. Lin, A. Hofmann, C. Lenczyk, S. Kachel, I. Krummenacher, Z. Lin and H. Braunschweig, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02032J

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