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Issue 10, 2013
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Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

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Abstract

S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow access to five, six and seven-membered alicyclic-ring fused heterocycles with and without an additional fused cyclopropane, including the skeleton of the anti-cancer agent, cyclopropamitosene, expanded, and diazole analogues. Radical initiators are not required for cyclisation from carboxylic acid precursors.

Graphical abstract: Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

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Publication details

The article was received on 28 Nov 2012, accepted on 22 Jan 2013 and first published on 23 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB27313J
Citation: Org. Biomol. Chem., 2013,11, 1672-1682
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    Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

    R. Coyle, K. Fahey and F. Aldabbagh, Org. Biomol. Chem., 2013, 11, 1672
    DOI: 10.1039/C3OB27313J

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