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 journalArticle

41 Citations (Scopus)
63 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)2564-2568
Number of pages5
JournalAngewandte Chemie-International Edition
Volume55
Issue number7
Early online date14 Jan 2016
DOIs
Publication statusPublished - 12 Feb 2016

Fingerprint

Salts
Azulenes
azulene

Keywords

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

Cite this

Azulenesulfonium salts : accessible, stable, and versatile reagents for cross-coupling. / Cowper, Paul; Jin, Yu; Turton, Michael D.; Kociok-Kohn, Gabriele; Lewis, Simon E.

In: Angewandte Chemie-International Edition, Vol. 55, No. 7, 12.02.2016, p. 2564-2568.

Research output: Contribution to journalArticle

@article{63a265d048df4f99bcc803668e9f487f,
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",
month = "2",
day = "12",
doi = "10.1002/anie.201510666",
language = "English",
volume = "55",
pages = "2564--2568",
journal = "Angewandte Chemie-International Edition",
issn = "1433-7851",
publisher = "WILEY-V C H VERLAG GMBH",
number = "7",

}

TY - JOUR

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

VL - 55

SP - 2564

EP - 2568

JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

SN - 1433-7851

IS - 7

ER -