A convenient metal-free reagent for the generation and capture of trifluoromethanethiol

Shi Guang Li; Samir Z. Zard

doi:10.1021/ol403038f

A convenient metal-free reagent for the generation and capture of trifluoromethanethiol

Shi Guang Li
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

90 Citations (Scopus)

Abstract

O-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium O-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with α-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.

Original language	English
Pages (from-to)	5898-5901
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	22
DOIs	https://doi.org/10.1021/ol403038f
Publication status	Published - 15 Nov 2013
Externally published	Yes

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10.1021/ol403038f

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title = "A convenient metal-free reagent for the generation and capture of trifluoromethanethiol",

abstract = "O-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium O-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with α-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.",

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year = "2013",

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journal = "Organic Letters",

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AU - Li, Shi Guang

AU - Zard, Samir Z.

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Y1 - 2013/11/15

N2 - O-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium O-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with α-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.

AB - O-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium O-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with α-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.

U2 - 10.1021/ol403038f

DO - 10.1021/ol403038f

M3 - Article

AN - SCOPUS:84887968929

SN - 1523-7060

VL - 15

SP - 5898

EP - 5901

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

A convenient metal-free reagent for the generation and capture of trifluoromethanethiol

Abstract

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