From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones.

Laurent Debien 1 Samir Z Zard 1
1 DCSO - Laboratoire de synthèse organique
Abstract : A new radical addition/C-C bond fragmentation process is reported. Vinyl carbinols derived from 2-methyl-2-phenylpropanal react with radicals generated from xanthates to give the corresponding ketones. The radical cleavage reaction proceeds under mild conditions, in good to high yield, and in the presence of the unprotected carbinol. Highly functionalized 1,5-diketones and pyridines are readily available using this approach.
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Submitted on : Wednesday, March 26, 2014 - 9:53:34 PM
Last modification on : Thursday, February 7, 2019 - 5:19:31 PM

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Laurent Debien, Samir Z Zard. From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones.. Journal of the American Chemical Society, American Chemical Society, 2013, 135 (10), pp.3808-3811. ⟨10.1021/ja400831w⟩. ⟨hal-00966618⟩

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