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Issue 5, 2015
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Development of zinc alkyl/air systems as radical initiators for organic reactions

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Abstract

This paper reports a series of comparative experiments on the activity of carbon- and oxygen-centred radical species in a model reaction of the radical addition of THF to imines mediated by a series of zinc alkyl/air reaction systems. The study strongly contradicts the notion that generally R˙ radicals are the initiating species in organic reactions mediated by RnM/air systems, and simultaneously demonstrates that oxygen-centred radical species are the key intermediates responsible for the initiation process. In addition, a new efficient RZn(L)/air initiating system for radical organic reactions exampled by a model reaction of radical addition of THF to imines is developed. Moreover, the isolation and structural characterization of the first zinc alkylperoxide supported by a carboxylate ligand, [Zn43-OOtBu)34-O)(O2CEt)3]2, as well as the novel octanuclear zinc oxo(alkoxide) aggregate with entrapped O–THF species, [Zn44-O)(μ3-2-O–THF)(O2CEt)5]2, provide clear mechanistic signatures for the mode of function of the RZn(O2CR′)/air system.

Graphical abstract: Development of zinc alkyl/air systems as radical initiators for organic reactions

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Article information


Submitted
16 Feb 2015
Accepted
19 Mar 2015
First published
19 Mar 2015

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

Chem. Sci., 2015,6, 3102-3108
Article type
Edge Article

Development of zinc alkyl/air systems as radical initiators for organic reactions

M. Kubisiak, K. Zelga, W. Bury, I. Justyniak, K. Budny-Godlewski, Z. Ochal and J. Lewiński, Chem. Sci., 2015, 6, 3102
DOI: 10.1039/C5SC00600G

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