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

John M. Halford-McGuff; Thomas M. Richardson; Aidan P. McKay; Frederik Peschke; Glenn A. Burley; Allan J. B. Watson

doi:10.3762/bjoc.20.265

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

John M. Halford-McGuff, Thomas M. Richardson, Aidan P. McKay, Frederik Peschke, Glenn A. Burley, Allan J. B. Watson

Pure And Applied Chemistry

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

2 Citations (Scopus)

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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

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 (RPG2020-380). 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.

Keywords

chemoselectivity
click chemistry
copper
germanium
triazole

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10.3762/bjoc.20.265Licence: CC BY 4.0

Halford-McGuff-etal-Germanyl-triazoles-as-a-platform-for-CuAAC-diversification-and-chemoselective-orthogonal-cross-couplingFinal published version, 401 KBLicence: CC BY 4.0

Cite this

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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.",

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AU - Halford-McGuff, John M.

AU - Richardson, Thomas M.

AU - McKay, Aidan P.

AU - Peschke, Frederik

AU - Burley, Glenn A.

AU - Watson, Allan J. B.

PY - 2024/12/5

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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

UR - https://doi.org/10.17630/53959471-068e-483e-bcd4-920e6761926b.

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DO - 10.3762/bjoc.20.265

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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

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