Ex-Situ Generation of Bis(trifluoromethyl)disulfide and Applications to Trifluoromethylthiolation Reactions

Iuliia Kolodiazhnaia; Haraldur Gunnar Guðmundsson; Simon Steffen Pedersen; Troels Skrydstrup

doi:10.1002/ejoc.202300843

Ex-Situ Generation of Bis(trifluoromethyl)disulfide and Applications to Trifluoromethylthiolation Reactions

Iuliia Kolodiazhnaia
, Haraldur Gunnar Guðmundsson^*
, Simon Steffen Pedersen
, Troels Skrydstrup^*

^*Corresponding author for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

2 Citations (Scopus)

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Abstract

Herein, a convenient and operationally simple protocol for the ex-situ generation of bis(trifluoromethyl)disulfide from the readily available and commercial Langlois reagent is reported. The one-step synthesis of the toxic and volatile CF3SSCF3 is performed in a two-chamber reactor with simple PPh3 and N-bromosuccinimide as the activator, allowing for the safe handling and tandem utilization in direct trifluoromethylthiolation reactions. The versatility of the ex-situ generated CF3SSCF3 is demonstrated in known electrophilic, nucleophilic, and a radical trifluoromethylthiolation reactions. Furthermore, the application of the CF3SSCF3 in a copper-catalyzed cross-coupling with boronic acids is disclosed, showing good to excellent yields of trifluoromethyl-substituted aryl products, including pharmaceutically relevant molecules.

Original language	English
Article number	e202300843
Journal	European Journal of Organic Chemistry
Volume	26
Issue	44
Number of pages	8
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.202300843
Publication status	Published - 21 Nov 2023

Keywords

copper catalysis
cross-coupling
disulfide
sulfenylation
trifluoromethylthiolation

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Eur J Org Chem - 2023 - Kolodiazhnaia - Ex‐Situ Generation of Bis trifluoromethyl disulfide and Applications toFinal published version, 4.73 MBLicence: CC BY-NC-ND

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title = "Ex-Situ Generation of Bis(trifluoromethyl)disulfide and Applications to Trifluoromethylthiolation Reactions",

abstract = "Herein, a convenient and operationally simple protocol for the ex-situ generation of bis(trifluoromethyl)disulfide from the readily available and commercial Langlois reagent is reported. The one-step synthesis of the toxic and volatile CF3SSCF3 is performed in a two-chamber reactor with simple PPh3 and N-bromosuccinimide as the activator, allowing for the safe handling and tandem utilization in direct trifluoromethylthiolation reactions. The versatility of the ex-situ generated CF3SSCF3 is demonstrated in known electrophilic, nucleophilic, and a radical trifluoromethylthiolation reactions. Furthermore, the application of the CF3SSCF3 in a copper-catalyzed cross-coupling with boronic acids is disclosed, showing good to excellent yields of trifluoromethyl-substituted aryl products, including pharmaceutically relevant molecules.",

keywords = "copper catalysis, cross-coupling, disulfide, sulfenylation, trifluoromethylthiolation",

author = "Iuliia Kolodiazhnaia and Gu{\dh}mundsson, \{Haraldur Gunnar\} and Pedersen, \{Simon Steffen\} and Troels Skrydstrup",

year = "2023",

month = nov,

day = "21",

doi = "10.1002/ejoc.202300843",

language = "English",

volume = "26",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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Ex-Situ Generation of Bis(trifluoromethyl)disulfide and Applications to Trifluoromethylthiolation Reactions. / Kolodiazhnaia, Iuliia; Guðmundsson, Haraldur Gunnar; Pedersen, Simon Steffen et al.
In: European Journal of Organic Chemistry, Vol. 26, No. 44, e202300843, 21.11.2023.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Ex-Situ Generation of Bis(trifluoromethyl)disulfide and Applications to Trifluoromethylthiolation Reactions

AU - Kolodiazhnaia, Iuliia

AU - Guðmundsson, Haraldur Gunnar

AU - Pedersen, Simon Steffen

AU - Skrydstrup, Troels

PY - 2023/11/21

Y1 - 2023/11/21

N2 - Herein, a convenient and operationally simple protocol for the ex-situ generation of bis(trifluoromethyl)disulfide from the readily available and commercial Langlois reagent is reported. The one-step synthesis of the toxic and volatile CF3SSCF3 is performed in a two-chamber reactor with simple PPh3 and N-bromosuccinimide as the activator, allowing for the safe handling and tandem utilization in direct trifluoromethylthiolation reactions. The versatility of the ex-situ generated CF3SSCF3 is demonstrated in known electrophilic, nucleophilic, and a radical trifluoromethylthiolation reactions. Furthermore, the application of the CF3SSCF3 in a copper-catalyzed cross-coupling with boronic acids is disclosed, showing good to excellent yields of trifluoromethyl-substituted aryl products, including pharmaceutically relevant molecules.

AB - Herein, a convenient and operationally simple protocol for the ex-situ generation of bis(trifluoromethyl)disulfide from the readily available and commercial Langlois reagent is reported. The one-step synthesis of the toxic and volatile CF3SSCF3 is performed in a two-chamber reactor with simple PPh3 and N-bromosuccinimide as the activator, allowing for the safe handling and tandem utilization in direct trifluoromethylthiolation reactions. The versatility of the ex-situ generated CF3SSCF3 is demonstrated in known electrophilic, nucleophilic, and a radical trifluoromethylthiolation reactions. Furthermore, the application of the CF3SSCF3 in a copper-catalyzed cross-coupling with boronic acids is disclosed, showing good to excellent yields of trifluoromethyl-substituted aryl products, including pharmaceutically relevant molecules.

KW - copper catalysis

KW - cross-coupling

KW - disulfide

KW - sulfenylation

KW - trifluoromethylthiolation

U2 - 10.1002/ejoc.202300843

DO - 10.1002/ejoc.202300843

M3 - Journal article

SN - 1434-193X

VL - 26

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 44

M1 - e202300843

ER -

Ex-Situ Generation of Bis(trifluoromethyl)disulfide and Applications to Trifluoromethylthiolation Reactions

Abstract

Keywords

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