A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones

Lucile Anthore; Samir Z. Zard

doi:10.1021/acs.orglett.5b01344

A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones

Lucile Anthore
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

A convergent synthesis of trifluoromethyl ketones and α,β-unsaturated trifluoromethyl ketones is described, starting with aliphatic iodides and dithiocarbonates (xanthates) and exploiting both the α- and β-fragmentations of a sulfonyl radical. The transformation initially furnishes the ketones in a masked enol carbonate form, from which they can be easily regenerated.

Original language	English
Pages (from-to)	3058-3061
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.5b01344
Publication status	Published - 19 Jun 2015
Externally published	Yes

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title = "A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones",

abstract = "A convergent synthesis of trifluoromethyl ketones and α,β-unsaturated trifluoromethyl ketones is described, starting with aliphatic iodides and dithiocarbonates (xanthates) and exploiting both the α- and β-fragmentations of a sulfonyl radical. The transformation initially furnishes the ketones in a masked enol carbonate form, from which they can be easily regenerated.",

author = "Lucile Anthore and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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AU - Anthore, Lucile

AU - Zard, Samir Z.

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Y1 - 2015/6/19

N2 - A convergent synthesis of trifluoromethyl ketones and α,β-unsaturated trifluoromethyl ketones is described, starting with aliphatic iodides and dithiocarbonates (xanthates) and exploiting both the α- and β-fragmentations of a sulfonyl radical. The transformation initially furnishes the ketones in a masked enol carbonate form, from which they can be easily regenerated.

AB - A convergent synthesis of trifluoromethyl ketones and α,β-unsaturated trifluoromethyl ketones is described, starting with aliphatic iodides and dithiocarbonates (xanthates) and exploiting both the α- and β-fragmentations of a sulfonyl radical. The transformation initially furnishes the ketones in a masked enol carbonate form, from which they can be easily regenerated.

U2 - 10.1021/acs.orglett.5b01344

DO - 10.1021/acs.orglett.5b01344

M3 - Article

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AN - SCOPUS:84934944820

SN - 1523-7060

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EP - 3061

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones

Abstract

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