Photocatalytic conversion of aryl diazonium salts to sulfonyl fluorides

Cooper A. Vincent; Alexia Ripak; Ludovic Troian-Gautier; Uttam K. Tambar

doi:10.1016/j.tet.2023.133364

Photocatalytic conversion of aryl diazonium salts to sulfonyl fluorides

Cooper A. Vincent, Alexia Ripak, Ludovic Troian-Gautier, Uttam K. Tambar

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

2 Scopus citations

Abstract

Sulfonyl fluorides have emerged as powerful tools in chemical biology for the selective labelling of proteins. A photocatalytic method is described for the conversion of aryl diazonium salts to aryl sulfonyl fluorides. The diazonium substrates are easily obtained in one step from functionalized anilines. We present the optimization of this mild method for the synthesis of sulfonyl fluorides, the scope of the transformation with a series of functionalized diazonium salts, and we discuss photophysical measurements that provide detailed information about the mechanism of the photochemical process.

Original language	English (US)
Article number	133364
Journal	Tetrahedron
Volume	139
DOIs	https://doi.org/10.1016/j.tet.2023.133364
State	Published - Jun 12 2023

Keywords

Diazonium salts
Electron transfer
Photocatalyst
Sulfonyl fluorides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2023.133364

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title = "Photocatalytic conversion of aryl diazonium salts to sulfonyl fluorides",

abstract = "Sulfonyl fluorides have emerged as powerful tools in chemical biology for the selective labelling of proteins. A photocatalytic method is described for the conversion of aryl diazonium salts to aryl sulfonyl fluorides. The diazonium substrates are easily obtained in one step from functionalized anilines. We present the optimization of this mild method for the synthesis of sulfonyl fluorides, the scope of the transformation with a series of functionalized diazonium salts, and we discuss photophysical measurements that provide detailed information about the mechanism of the photochemical process.",

keywords = "Diazonium salts, Electron transfer, Photocatalyst, Sulfonyl fluorides",

author = "Vincent, {Cooper A.} and Alexia Ripak and Ludovic Troian-Gautier and Tambar, {Uttam K.}",

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T1 - Photocatalytic conversion of aryl diazonium salts to sulfonyl fluorides

AU - Vincent, Cooper A.

AU - Ripak, Alexia

AU - Troian-Gautier, Ludovic

AU - Tambar, Uttam K.

PY - 2023/6/12

Y1 - 2023/6/12

N2 - Sulfonyl fluorides have emerged as powerful tools in chemical biology for the selective labelling of proteins. A photocatalytic method is described for the conversion of aryl diazonium salts to aryl sulfonyl fluorides. The diazonium substrates are easily obtained in one step from functionalized anilines. We present the optimization of this mild method for the synthesis of sulfonyl fluorides, the scope of the transformation with a series of functionalized diazonium salts, and we discuss photophysical measurements that provide detailed information about the mechanism of the photochemical process.

AB - Sulfonyl fluorides have emerged as powerful tools in chemical biology for the selective labelling of proteins. A photocatalytic method is described for the conversion of aryl diazonium salts to aryl sulfonyl fluorides. The diazonium substrates are easily obtained in one step from functionalized anilines. We present the optimization of this mild method for the synthesis of sulfonyl fluorides, the scope of the transformation with a series of functionalized diazonium salts, and we discuss photophysical measurements that provide detailed information about the mechanism of the photochemical process.

KW - Diazonium salts

KW - Electron transfer

KW - Photocatalyst

KW - Sulfonyl fluorides

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JO - Tetrahedron

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Photocatalytic conversion of aryl diazonium salts to sulfonyl fluorides

Abstract

Keywords

ASJC Scopus subject areas

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