Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling

John Halford-McGuff; Thomas Richardson; Aidan McKay; Frederik Peschke; Glenn Burley; Allan John Bell Watson

doi:10.3762/bjoc.20.265

Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling

John Halford-McGuff, Thomas Richardson, Aidan McKay, Frederik Peschke, Glenn Burley^*, Allan John Bell Watson^*

^*Corresponding author for this work

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

Abstract

We report the synthesis of germanyl triazoles formed via a copper-catalysed azide–alkyne cycloaddition (CuAAC) of germanyl alkynes. The reaction is often high yielding, functional group tolerant, and compatible with complex molecules. The installation of the Ge moiety enables further diversification of the triazole products, including chemoselective transition metal-catalysed cross-coupling reactions using bifunctional boryl/germyl species.

Original language	English
Pages (from-to)	3198–3204
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	20
DOIs	https://doi.org/10.3762/bjoc.20.265
Publication status	Published - 5 Dec 2024

Keywords

chemoselectivity
click chemistry
copper
germanium
triazole

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1 Active
2 Finished

Allan Watson Programme Grant: Boron: Beyond the Reagent
Watson, A. J. B. (PI), Morris, R. E. (CoI), Smith, A. D. (CoI) & Zysman-Colman, E. (CoI)
UK Research and Innovation
1/05/23 → 30/04/28
Project: Standard
A biochemical boron tagging stategy: A biochemical boron tagging strategy for biomolecule visualisation and profiling
Watson, A. J. B. (PI)
The Leverhulme Trust
1/09/22 → 31/08/24
Project: Fellowship
A Unified Approach to Bio-orthogonal: A Unified Approach to Bio-orthogonal Reaction Discovery in Living systems
Watson, A. J. B. (PI)
The Leverhulme Trust
1/06/21 → 30/11/23
Project: Standard

Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling (dataset)
Watson, A. J. B. (Creator), University of St Andrews, 6 Dec 2024
DOI: 10.17630/53959471-068e-483e-bcd4-920e6761926b
Dataset

File

Cite this

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title = "Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling",

abstract = "We report the synthesis of germanyl triazoles formed via a copper-catalysed azide–alkyne cycloaddition (CuAAC) of germanyl alkynes. The reaction is often high yielding, functional group tolerant, and compatible with complex molecules. The installation of the Ge moiety enables further diversification of the triazole products, including chemoselective transition metal-catalysed cross-coupling reactions using bifunctional boryl/germyl species.",

keywords = "chemoselectivity, click chemistry, copper, germanium, triazole",

author = "John Halford-McGuff and Thomas Richardson and Aidan McKay and Frederik Peschke and Glenn Burley and Watson, {Allan John Bell}",

note = "Funding: J.M.H.-M. thanks the EPSRC Centre for Doctoral Training EaSI-CAT for a Ph.D. studentship. T.M.R. thanks the EPSRC and the University of St Andrews for Ph.D. studentship. G.A.B., F.P., and A.J.B.W. thank the Leverhulme Trust (RPG-2020-380). A.J.B.W. thanks the Leverhulme Trust for a Research Fellowship (RF-2022-014) and the EPSRC Programme Grant {\textquoteleft}{\textquoteleft}Boron: Beyond the Reagent{\textquoteright}{\textquoteright} (EP/W007517/1) for support.",

year = "2024",

month = dec,

day = "5",

doi = "10.3762/bjoc.20.265",

language = "English",

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TY - JOUR

T1 - Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling

AU - Halford-McGuff, John

AU - Richardson, Thomas

AU - McKay, Aidan

AU - Peschke, Frederik

AU - Burley, Glenn

AU - Watson, Allan John Bell

N1 - Funding: J.M.H.-M. thanks the EPSRC Centre for Doctoral Training EaSI-CAT for a Ph.D. studentship. T.M.R. thanks the EPSRC and the University of St Andrews for Ph.D. studentship. G.A.B., F.P., and A.J.B.W. thank the Leverhulme Trust (RPG-2020-380). A.J.B.W. thanks the Leverhulme Trust for a Research Fellowship (RF-2022-014) and the EPSRC Programme Grant ‘‘Boron: Beyond the Reagent’’ (EP/W007517/1) for support.

PY - 2024/12/5

Y1 - 2024/12/5

N2 - We report the synthesis of germanyl triazoles formed via a copper-catalysed azide–alkyne cycloaddition (CuAAC) of germanyl alkynes. The reaction is often high yielding, functional group tolerant, and compatible with complex molecules. The installation of the Ge moiety enables further diversification of the triazole products, including chemoselective transition metal-catalysed cross-coupling reactions using bifunctional boryl/germyl species.

AB - We report the synthesis of germanyl triazoles formed via a copper-catalysed azide–alkyne cycloaddition (CuAAC) of germanyl alkynes. The reaction is often high yielding, functional group tolerant, and compatible with complex molecules. The installation of the Ge moiety enables further diversification of the triazole products, including chemoselective transition metal-catalysed cross-coupling reactions using bifunctional boryl/germyl species.

KW - chemoselectivity

KW - click chemistry

KW - copper

KW - germanium

KW - triazole

U2 - 10.3762/bjoc.20.265

DO - 10.3762/bjoc.20.265

M3 - Article

SN - 1860-5397

VL - 20

SP - 3198

EP - 3204

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling

Abstract

Keywords

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Projects

Allan Watson Programme Grant: Boron: Beyond the Reagent

A biochemical boron tagging stategy: A biochemical boron tagging strategy for biomolecule visualisation and profiling

A Unified Approach to Bio-orthogonal: A Unified Approach to Bio-orthogonal Reaction Discovery in Living systems

Datasets

Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling (dataset)

Cite this