General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition

Paul Davies; Miguel Garzon Sanz; Elsa Martinez Arce; Raju Jannapureddy

doi:10.1002/adsc.201700249

General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition

Paul Davies, Miguel Garzon Sanz, Elsa Martinez Arce, Raju Jannapureddy

Chemistry

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

14 Citations (Scopus)

270 Downloads (Pure)

Abstract

A general redox-neutral approach into the o-,o’-heteroatom-linked N-(hetero)aryl imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench-stable N-(heteroaryl) pyridinium N-aminides by formal gold-catalysed [3+2]-dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.

Original language	English
Journal	Advanced Synthesis & Catalysis
Early online date	18 Apr 2017
DOIs	https://doi.org/10.1002/adsc.201700249
Publication status	E-pub ahead of print - 18 Apr 2017

Keywords

cycloaddition
nucleophilic nitrenoids
dipoles
gold
nitrogen heterocycles

ASJC Scopus subject areas

General Chemistry
Organic Chemistry

Access to Document

10.1002/adsc.201700249Licence: None: All rights reserved

Garz-n_et_al-2017-Advanced_Synthesis_&_Catalysis
This is the peer reviewed version of the following article: Garzón, M., Arce, E., Jannapu Reddy, R. and Davies, P. (2017), General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition. Adv. Synth. Catal.. Accepted Author Manuscript. doi:10.1002/adsc.201700249, which has been published in final form at doi:10.1002/adsc.201700249. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Accepted author manuscript, 2.12 MBLicence: Other (please specify with Rights Statement)

14 Citations
5 Article
1 Review 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
95 Downloads (Pure)
Sulfenyl ynamides in gold catalysis: synthesis of oxo‐functionalised 4‐aminoimidazolyl fused compounds by intermolecular annulation reactions
Arce, E. M., Lamont, S. G. & Davies, P. W., 15 Jun 2020, In: Advanced Synthesis & Catalysis. 362, 12, p. 2503-2509 7 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
5 Citations (Scopus)

174 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)

176 Downloads (Pure)
Efficient and flexible synthesis of highly functionalised 4-aminooxazoles by a gold-catalysed intermolecular formal [3+2]-dipolar cycloaddition
Davies, P., Gillie, A. & Jannapureddy, R., 21 Jan 2016, In: Advanced Synthesis & Catalysis. 358, 2, p. 226-239
Research output: Contribution to journal › Article › peer-review

Open Access
53 Citations (Scopus)
Nucleophilic nitrenoids through π-acid catalysis: providing a common basis for rapid access into diverse nitrogen heterocycles
Davies, P. & Garzon Sanz, M., Aug 2015, In: Asian Journal of Organic Chemistry. 4, 8, p. 694-708 15 p.
Research output: Contribution to journal › Review article › peer-review

Open Access
File
76 Citations (Scopus)

297 Downloads (Pure)
A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition
Garzon, M. & Davies, P. W., 19 Sept 2014, In: Organic Letters. 16, 18, p. 4850-3 4 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
62 Citations (Scopus)

232 Downloads (Pure)

2 Finished

Studentship - Elsa Martinez Arce - Umpolung N-nucleophilic nitrene character of N,N-ylides
Davies, P. (Principal Investigator)
ASTRA ZENECA UK LIMITED
29/09/14 → 28/03/18
Project: Industry
FP7 MC IIF: SynHet - Convergent and Efficient Synthesis of Novel Heteroaromatics
Davies, P. (Principal Investigator)
European Commission
21/01/13 → 20/01/15
Project: EU

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

Cite this

@article{5b10eb5a27564ad2ad97d8e332ae931a,

title = "General Entry into o-,o{\textquoteright}-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition",

abstract = "A general redox-neutral approach into the o-,o{\textquoteright}-heteroatom-linked N-(hetero)aryl imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench-stable N-(heteroaryl) pyridinium N-aminides by formal gold-catalysed [3+2]-dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.",

keywords = "cycloaddition, nucleophilic nitrenoids, dipoles, gold, nitrogen heterocycles",

author = "Paul Davies and {Garzon Sanz}, Miguel and {Martinez Arce}, Elsa and Raju Jannapureddy",

year = "2017",

month = apr,

day = "18",

doi = "10.1002/adsc.201700249",

language = "English",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4169",

publisher = "Wiley-VCH Verlag",

}

TY - JOUR

T1 - General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition

AU - Davies, Paul

AU - Garzon Sanz, Miguel

AU - Martinez Arce, Elsa

AU - Jannapureddy, Raju

PY - 2017/4/18

Y1 - 2017/4/18

N2 - A general redox-neutral approach into the o-,o’-heteroatom-linked N-(hetero)aryl imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench-stable N-(heteroaryl) pyridinium N-aminides by formal gold-catalysed [3+2]-dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.

AB - A general redox-neutral approach into the o-,o’-heteroatom-linked N-(hetero)aryl imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench-stable N-(heteroaryl) pyridinium N-aminides by formal gold-catalysed [3+2]-dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.

KW - cycloaddition

KW - nucleophilic nitrenoids

KW - dipoles

KW - gold

KW - nitrogen heterocycles

U2 - 10.1002/adsc.201700249

DO - 10.1002/adsc.201700249

M3 - Article

SN - 1615-4169

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

ER -

General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Research output

Projects

Equipment

Cite this