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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3808-3811
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	10
DOIs	https://doi.org/10.1021/ja400831w
Publication status	Published - 13 Mar 2013
Externally published	Yes

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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",

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journal = "Journal of the American Chemical Society",

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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

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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

Abstract

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