Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Paul Davies; Richard Grainger; Matthew Barrett

doi:10.1039/C5OB01241D

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Paul Davies
, Richard Grainger
, Matthew Barrett

Chemistry

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

17 Citations (Scopus)

232 Downloads (Pure)

Abstract

A protocol has been developed for direct Csp3-Csp2 bond formation at the 4- and 6-positions of dibenzothiophenes using a gold(I) catalyst with terminal alkynes and dibenzothiophene-S-oxides. The sulfoxide acts as a traceless directing group to avoid the need to prefunctionalise at carbon. The iterative use of this protocol is possible and has been employed in the preparation of novel macrocyclic structures. In addition, a cascade process shows how oxyarylations can be combined with other processes resulting in complex, highly efficient transformations.

Original language	English
Pages (from-to)	8676-8686
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	32
Early online date	7 Jul 2015
DOIs	https://doi.org/10.1039/C5OB01241D
Publication status	Published - 28 Aug 2015

Access to Document

10.1039/C5OB01241D

Barrett_et_al_Regioselective_functionalisation_Organic_Biomolecular_Chemistry_2015
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Checked July 2015
Final published version, 621 KBLicence: Creative Commons: Attribution (CC BY)

Gold-catalyzed intermolecular alkyne oxyarylation for C3-functionalization of benzothiophenes
Rist, P., Grainger, R. & Davies, P., 5 Feb 2021, In: Organic Letters. 23, 3, p. 642–646 5 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
292 Downloads (Pure)
Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation
Barrett, M., Khan, G., Davies, P. & Grainger, R., 25 May 2017, In: Chemical Communications . 53, 42, p. 5733-5736 4 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
20 Citations (Scopus)

254 Downloads (Pure)

Birmingham Environment for Academic Research (BEAR)
Facility/equipment: Equipment

Cite this

@article{a21f0ca64a904935a12d56bd41ab635f,

title = "Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation",

abstract = "A protocol has been developed for direct Csp3-Csp2 bond formation at the 4- and 6-positions of dibenzothiophenes using a gold(I) catalyst with terminal alkynes and dibenzothiophene-S-oxides. The sulfoxide acts as a traceless directing group to avoid the need to prefunctionalise at carbon. The iterative use of this protocol is possible and has been employed in the preparation of novel macrocyclic structures. In addition, a cascade process shows how oxyarylations can be combined with other processes resulting in complex, highly efficient transformations.",

author = "Paul Davies and Richard Grainger and Matthew Barrett",

year = "2015",

month = aug,

day = "28",

doi = "10.1039/C5OB01241D",

language = "English",

volume = "13",

pages = "8676--8686",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "32",

}

TY - JOUR

T1 - Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

AU - Davies, Paul

AU - Grainger, Richard

AU - Barrett, Matthew

PY - 2015/8/28

Y1 - 2015/8/28

N2 - A protocol has been developed for direct Csp3-Csp2 bond formation at the 4- and 6-positions of dibenzothiophenes using a gold(I) catalyst with terminal alkynes and dibenzothiophene-S-oxides. The sulfoxide acts as a traceless directing group to avoid the need to prefunctionalise at carbon. The iterative use of this protocol is possible and has been employed in the preparation of novel macrocyclic structures. In addition, a cascade process shows how oxyarylations can be combined with other processes resulting in complex, highly efficient transformations.

AB - A protocol has been developed for direct Csp3-Csp2 bond formation at the 4- and 6-positions of dibenzothiophenes using a gold(I) catalyst with terminal alkynes and dibenzothiophene-S-oxides. The sulfoxide acts as a traceless directing group to avoid the need to prefunctionalise at carbon. The iterative use of this protocol is possible and has been employed in the preparation of novel macrocyclic structures. In addition, a cascade process shows how oxyarylations can be combined with other processes resulting in complex, highly efficient transformations.

U2 - 10.1039/C5OB01241D

DO - 10.1039/C5OB01241D

M3 - Article

C2 - 26177794

SN - 1477-0520

VL - 13

SP - 8676

EP - 8686

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 32

ER -

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

Abstract

Access to Document

Fingerprint

Research output

Gold-catalyzed intermolecular alkyne oxyarylation for C3-functionalization of benzothiophenes

Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation

Equipment

Birmingham Environment for Academic Research (BEAR)

Cite this