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

Laurent Debien; Samir Z. Zard

doi:10.1021/ja400831w

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

Laurent Debien
, Samir Z. Zard

Laboratoire de Synthèse Organique

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	3808-3811
Nombre de pages	4
journal	Journal of the American Chemical Society
Volume	135
Numéro de publication	10
Les DOIs	https://doi.org/10.1021/ja400831w
état	Publié - 13 mars 2013
Modification externe	Oui

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10.1021/ja400831w

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title = "From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones",

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.",

author = "Laurent Debien and Zard, \{Samir Z.\}",

year = "2013",

month = mar,

day = "13",

doi = "10.1021/ja400831w",

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journal = "Journal of the American Chemical Society",

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AU - Debien, Laurent

AU - Zard, Samir Z.

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N2 - 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.

AB - 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.

U2 - 10.1021/ja400831w

DO - 10.1021/ja400831w

M3 - Article

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AN - SCOPUS:84874954772

SN - 0002-7863

VL - 135

SP - 3808

EP - 3811

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 10

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

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