Azulenesulfonium salts: accessible, stable, and versatile reagents for cross-coupling

Paul Cowper; Yu Jin; Michael D. Turton; Gabriele Kociok-Kohn; Simon E. Lewis

doi:10.1002/anie.201510666

Azulenesulfonium salts: accessible, stable, and versatile reagents for cross-coupling

Paul Cowper, Yu Jin, Michael D. Turton, Gabriele Kociok-Kohn, Simon E. Lewis

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

109 Citations (SciVal)

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Abstract

Azulenesulfonium salts may be readily prepared from the corresponding azulenes by an S_EAr reaction. These azulene sulfonium salts are bench-stable species that may be employed as pseudohalides for cross-coupling. Specifically, their application in Suzuki-Miyaura reactions has been demonstrated with a diverse selection of coupling partners. These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides, which are known to be unstable and difficult to prepare in pure form.

Original language	English
Pages (from-to)	2564-2568
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	7
Early online date	14 Jan 2016
DOIs	https://doi.org/10.1002/anie.201510666
Publication status	Published - 12 Feb 2016

Keywords

Azulenes
Sulfonium salts
Sulfoxides
Suzuki-Miyaura cross-coupling
Synthetic methods

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10.1002/anie.201510666Licence: CC BY

Supporting Research Excellence in Chemistry at the University of Bath through Provision of Key Equipment Enhancements
Wilson, C. (PI), Lowe, J. (CoI), Lubben, A. T. (CoI), Mahon, M. (CoI) & Raithby, P. (CoI)
Engineering and Physical Sciences Research Council
11/03/14 → 10/06/14
Project: Research council

Simon Lewis
- S.E.Lewisbath.acuk
Person: Research & Teaching, Core staff

MC2-Mass Spectrometry (MS)
Material and Chemical Characterisation (MC2)
Facility/equipment: Technology type
MC2- Nuclear Magnetic Resonance (NMR)
Material and Chemical Characterisation (MC2)
Facility/equipment: Technology type
MC2- X-ray diffraction (XRD)
Material and Chemical Characterisation (MC2)
Facility/equipment: Technology type

Cite this

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title = "Azulenesulfonium salts: accessible, stable, and versatile reagents for cross-coupling",

abstract = "Azulenesulfonium salts may be readily prepared from the corresponding azulenes by an SEAr reaction. These azulene sulfonium salts are bench-stable species that may be employed as pseudohalides for cross-coupling. Specifically, their application in Suzuki-Miyaura reactions has been demonstrated with a diverse selection of coupling partners. These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides, which are known to be unstable and difficult to prepare in pure form.",

keywords = "Azulenes, Sulfonium salts, Sulfoxides, Suzuki-Miyaura cross-coupling, Synthetic methods",

author = "Paul Cowper and Yu Jin and Turton, {Michael D.} and Gabriele Kociok-Kohn and Lewis, {Simon E.}",

year = "2016",

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journal = "Angewandte Chemie International Edition",

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T1 - Azulenesulfonium salts

T2 - accessible, stable, and versatile reagents for cross-coupling

AU - Cowper, Paul

AU - Jin, Yu

AU - Turton, Michael D.

AU - Kociok-Kohn, Gabriele

AU - Lewis, Simon E.

PY - 2016/2/12

Y1 - 2016/2/12

N2 - Azulenesulfonium salts may be readily prepared from the corresponding azulenes by an SEAr reaction. These azulene sulfonium salts are bench-stable species that may be employed as pseudohalides for cross-coupling. Specifically, their application in Suzuki-Miyaura reactions has been demonstrated with a diverse selection of coupling partners. These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides, which are known to be unstable and difficult to prepare in pure form.

AB - Azulenesulfonium salts may be readily prepared from the corresponding azulenes by an SEAr reaction. These azulene sulfonium salts are bench-stable species that may be employed as pseudohalides for cross-coupling. Specifically, their application in Suzuki-Miyaura reactions has been demonstrated with a diverse selection of coupling partners. These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides, which are known to be unstable and difficult to prepare in pure form.

KW - Azulenes

KW - Sulfonium salts

KW - Sulfoxides

KW - Suzuki-Miyaura cross-coupling

KW - Synthetic methods

U2 - 10.1002/anie.201510666

DO - 10.1002/anie.201510666

M3 - Article

AN - SCOPUS:84954286621

SN - 1433-7851

VL - 55

SP - 2564

EP - 2568

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 7

ER -

Azulenesulfonium salts: accessible, stable, and versatile reagents for cross-coupling

Abstract

Keywords

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Supporting Research Excellence in Chemistry at the University of Bath through Provision of Key Equipment Enhancements

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Simon Lewis

Equipment

MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

MC2- X-ray diffraction (XRD)

Cite this