A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

Andrew D Gillie; Matthew G Wakeling; Bethan L Greene; Louise Male; Paul W Davies

doi:10.3762/bjoc.20.54

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

Andrew D Gillie, Matthew G Wakeling, Bethan L Greene, Louise Male, Paul W Davies^*

^*Corresponding author for this work

Chemistry

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

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Abstract

A polysubstituted 3-aminoimidazo[5,1-b]oxazol-6-ium framework has been accessed from a new nitrenoid reagent by a two-step ynamide annulation and imidazolium ring-formation sequence. Metalation with Au(I), Cu(I) and Ir(I) at the C2 position provides an L-shaped NHC ligand scaffold that has been validated in gold-catalysed alkyne hydration and arylative cyclisation reactions.

Original language	English
Pages (from-to)	621–627
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	20
DOIs	https://doi.org/10.3762/bjoc.20.54
Publication status	Published - 18 Mar 2024

Bibliographical note

Funding:
We thank EPSRC and the School of Chemistry at the University of Birmingham for studentship support (ADG, MGW, BLG). P.W.D. is grateful to the Royal Society and Leverhulme Trust for the award of a Senior Research Fellowship (SRF\R1\191033).

Keywords

annulation
carbene
gold
imidazolium
NHC

Access to Document

10.3762/bjoc.20.54Licence: Creative Commons: Attribution (CC BY)

GillieA2024laterallyFinal published version, 898 KBLicence: Creative Commons: Attribution (CC BY)

A mechanistic investigation into sulfur-enabled reactivity
Davies, P. (Principal Investigator)
The Royal Society
28/01/20 → 27/07/21
Project: Research Councils

Research data supporting the publication "A laterally-fused N-heterocyclic carbene framework from amino-imidazo[5,1-b]oxazol-6-ium salts"
Gillie, A. (Creator), Wakeling, M. (Creator), Greene, B. (Creator), Male, L. (Creator) & Davies, P. (Creator), University of Birmingham, 18 Dec 2023
DOI: 10.25500/edata.bham.00001041
Dataset

Cite this

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title = "A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts",

abstract = "A polysubstituted 3-aminoimidazo[5,1-b]oxazol-6-ium framework has been accessed from a new nitrenoid reagent by a two-step ynamide annulation and imidazolium ring-formation sequence. Metalation with Au(I), Cu(I) and Ir(I) at the C2 position provides an L-shaped NHC ligand scaffold that has been validated in gold-catalysed alkyne hydration and arylative cyclisation reactions.",

keywords = "annulation, carbene, gold, imidazolium, NHC",

author = "Gillie, {Andrew D} and Wakeling, {Matthew G} and Greene, {Bethan L} and Louise Male and Davies, {Paul W}",

note = "Funding: We thank EPSRC and the School of Chemistry at the University of Birmingham for studentship support (ADG, MGW, BLG). P.W.D. is grateful to the Royal Society and Leverhulme Trust for the award of a Senior Research Fellowship (SRF\R1\191033). ",

year = "2024",

month = mar,

day = "18",

doi = "10.3762/bjoc.20.54",

language = "English",

volume = "20",

pages = "621–627",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut",

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TY - JOUR

T1 - A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

AU - Gillie, Andrew D

AU - Wakeling, Matthew G

AU - Greene, Bethan L

AU - Male, Louise

AU - Davies, Paul W

N1 - Funding: We thank EPSRC and the School of Chemistry at the University of Birmingham for studentship support (ADG, MGW, BLG). P.W.D. is grateful to the Royal Society and Leverhulme Trust for the award of a Senior Research Fellowship (SRF\R1\191033).

PY - 2024/3/18

Y1 - 2024/3/18

N2 - A polysubstituted 3-aminoimidazo[5,1-b]oxazol-6-ium framework has been accessed from a new nitrenoid reagent by a two-step ynamide annulation and imidazolium ring-formation sequence. Metalation with Au(I), Cu(I) and Ir(I) at the C2 position provides an L-shaped NHC ligand scaffold that has been validated in gold-catalysed alkyne hydration and arylative cyclisation reactions.

AB - A polysubstituted 3-aminoimidazo[5,1-b]oxazol-6-ium framework has been accessed from a new nitrenoid reagent by a two-step ynamide annulation and imidazolium ring-formation sequence. Metalation with Au(I), Cu(I) and Ir(I) at the C2 position provides an L-shaped NHC ligand scaffold that has been validated in gold-catalysed alkyne hydration and arylative cyclisation reactions.

KW - annulation

KW - carbene

KW - gold

KW - imidazolium

KW - NHC

U2 - 10.3762/bjoc.20.54

DO - 10.3762/bjoc.20.54

M3 - Article

SN - 1860-5397

VL - 20

SP - 621

EP - 627

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

Abstract

Bibliographical note

Keywords

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Projects

A mechanistic investigation into sulfur-enabled reactivity

Datasets

Research data supporting the publication "A laterally-fused N-heterocyclic carbene framework from amino-imidazo[5,1-b]oxazol-6-ium salts"

Cite this