Gold(I)-catalyzed synthesis of 3-sulfenyl pyrroles and indoles by a regioselective annulation of alkynyl thioethers

Peter Simm; Prakash Sekar; Jeffery Richardson; Paul Davies

doi:10.1021/acscatal.1c01457

Gold(I)-catalyzed synthesis of 3-sulfenyl pyrroles and indoles by a regioselective annulation of alkynyl thioethers

Peter Simm, Prakash Sekar, Jeffery Richardson, Paul Davies

Chemistry

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

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Abstract

The combination of nucleophilic nitrenoids and π-acid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition β to the sulfenyl group. The reaction with isoxazole-containing nitrenoids delivers sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety.

Original language	English
Pages (from-to)	6357–6362
Number of pages	6
Journal	ACS Catalysis
Volume	11
Issue number	11
Early online date	13 May 2021
DOIs	https://doi.org/10.1021/acscatal.1c01457
Publication status	Published - 4 Jun 2021

Bibliographical note

Funding Information:
We thank the EPSRC and Eli Lilly for funding (NPIF studentship EP/R512436/1, P.E.S.). This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No. 839037 (P.S., SEAROX). P.W.D. is grateful to the Royal Society and Leverhulme Trust for the award of a Senior Research Fellowship (SRF\R1\191033). The authors gratefully acknowledge support from Dr. Louise Male (XRD) and the Centre for Chemical and Materials Analysis in the School of Chemistry (UoB).

Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society.

Keywords

annulation
gold
indole
nitrenoid
pyrroles
thioether

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1021/acscatal.1c01457Licence: Creative Commons: Attribution (CC BY)

SimmP2021GoldFinal published version, 1.44 MBLicence: Creative Commons: Attribution (CC BY)

2 Article

Gold-catalyzed annulations with nucleophilic nitrenoids enabled by heteroatom-substituted alkynes
Davies, P., 27 Oct 2021, (E-pub ahead of print) In: The Chemical Record. 21, 12, p. 3964-3977
Research output: Contribution to journal › Article › peer-review

Open Access
File
34 Downloads (Pure)
Alkynyl Thioethers in Gold-Catalyzed Annulations to form Oxazoles
Davies, P., Jannapu Reddy, R. & Ball-Jones, M., 16 Oct 2017, In: Angewandte Chemie (International Edition) . 56, 43, p. 13310–13313
Research output: Contribution to journal › Article › peer-review

Open Access
File
58 Citations (Scopus)

161 Downloads (Pure)

3 Finished

A mechanistic investigation into sulfur-enabled reactivity
Davies, P.
The Royal Society
28/01/20 → 27/07/21
Project: Research Councils
H2020_IF_SEAROX
Davies, P.
European Commission
7/08/19 → 6/08/21
Project: EU
To Conduct an Investigation on a Novel Catalysis-based Approach to Access Functionalised Heterocyclic Scaffolds
Davies, P.
ELI LILLY AND COMPANY
1/10/17 → 1/11/22
Project: Research

Research data supporting the publication "Gold(I)-Catalyzed Synthesis of 3‑Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers"
Simm, P. (Creator), Sekar, P. (Creator) & Davies, P. (Creator), University of Birmingham, 26 May 2021
DOI: https://doi.org/10.25500/edata.bham.00000661
Dataset

Cite this

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title = "Gold(I)-catalyzed synthesis of 3-sulfenyl pyrroles and indoles by a regioselective annulation of alkynyl thioethers",

abstract = "The combination of nucleophilic nitrenoids and π-acid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition β to the sulfenyl group. The reaction with isoxazole-containing nitrenoids delivers sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety.",

keywords = "annulation, gold, indole, nitrenoid, pyrroles, thioether",

author = "Peter Simm and Prakash Sekar and Jeffery Richardson and Paul Davies",

note = "Funding Information: We thank the EPSRC and Eli Lilly for funding (NPIF studentship EP/R512436/1, P.E.S.). This project has received funding from the European Union{\textquoteright}s Horizon 2020 research and innovation programme under the Marie Sk{\l}odowska-Curie grant agreement No. 839037 (P.S., SEAROX). P.W.D. is grateful to the Royal Society and Leverhulme Trust for the award of a Senior Research Fellowship (SRF\R1\191033). The authors gratefully acknowledge support from Dr. Louise Male (XRD) and the Centre for Chemical and Materials Analysis in the School of Chemistry (UoB). Publisher Copyright: {\textcopyright} 2021 The Authors. Published by American Chemical Society.",

year = "2021",

month = jun,

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doi = "10.1021/acscatal.1c01457",

language = "English",

volume = "11",

pages = "6357–6362",

journal = "ACS Catalysis",

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AU - Sekar, Prakash

AU - Richardson, Jeffery

AU - Davies, Paul

N1 - Funding Information: We thank the EPSRC and Eli Lilly for funding (NPIF studentship EP/R512436/1, P.E.S.). This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No. 839037 (P.S., SEAROX). P.W.D. is grateful to the Royal Society and Leverhulme Trust for the award of a Senior Research Fellowship (SRF\R1\191033). The authors gratefully acknowledge support from Dr. Louise Male (XRD) and the Centre for Chemical and Materials Analysis in the School of Chemistry (UoB). Publisher Copyright: © 2021 The Authors. Published by American Chemical Society.

PY - 2021/6/4

Y1 - 2021/6/4

N2 - The combination of nucleophilic nitrenoids and π-acid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition β to the sulfenyl group. The reaction with isoxazole-containing nitrenoids delivers sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety.

AB - The combination of nucleophilic nitrenoids and π-acid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition β to the sulfenyl group. The reaction with isoxazole-containing nitrenoids delivers sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety.

KW - annulation

KW - gold

KW - indole

KW - nitrenoid

KW - pyrroles

KW - thioether

UR - http://www.scopus.com/inward/record.url?scp=85106479140&partnerID=8YFLogxK

U2 - 10.1021/acscatal.1c01457

DO - 10.1021/acscatal.1c01457

M3 - Letter

SN - 2155-5435

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EP - 6362

JO - ACS Catalysis

JF - ACS Catalysis

IS - 11

ER -

Gold(I)-catalyzed synthesis of 3-sulfenyl pyrroles and indoles by a regioselective annulation of alkynyl thioethers

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Research output

Gold-catalyzed annulations with nucleophilic nitrenoids enabled by heteroatom-substituted alkynes

Alkynyl Thioethers in Gold-Catalyzed Annulations to form Oxazoles

Projects

A mechanistic investigation into sulfur-enabled reactivity

H2020_IF_SEAROX

To Conduct an Investigation on a Novel Catalysis-based Approach to Access Functionalised Heterocyclic Scaffolds

Datasets

Research data supporting the publication "Gold(I)-Catalyzed Synthesis of 3‑Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers"

Cite this