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

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...

Full description

Saved in:
Bibliographic Details
Main Authors: John M. Halford-McGuff, Thomas M. Richardson, Aidan P. McKay, Frederik Peschke, Glenn A. Burley, Allan J. B. Watson
Format: Article
Language:English
Published: Beilstein-Institut 2024-12-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.20.265
Tags: Add Tag
No Tags, Be the first to tag this record!
_version_ 1841557358687289344
author John M. Halford-McGuff
Thomas M. Richardson
Aidan P. McKay
Frederik Peschke
Glenn A. Burley
Allan J. B. Watson
author_facet John M. Halford-McGuff
Thomas M. Richardson
Aidan P. McKay
Frederik Peschke
Glenn A. Burley
Allan J. B. Watson
author_sort John M. Halford-McGuff
collection DOAJ
description 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.
format Article
id doaj-art-70aeffa2069f4dd7ad0aeffc6cbd1c79
institution Kabale University
issn 1860-5397
language English
publishDate 2024-12-01
publisher Beilstein-Institut
record_format Article
series Beilstein Journal of Organic Chemistry
spelling doaj-art-70aeffa2069f4dd7ad0aeffc6cbd1c792025-01-06T12:27:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-12-012013198320410.3762/bjoc.20.2651860-5397-20-265Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-couplingJohn M. Halford-McGuff0Thomas M. Richardson1Aidan P. McKay2Frederik Peschke3Glenn A. Burley4Allan J. B. Watson5EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK Department of Pure & Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK Department of Pure & Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK 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.https://doi.org/10.3762/bjoc.20.265chemoselectivityclick chemistrycoppergermaniumtriazole
spellingShingle John M. Halford-McGuff
Thomas M. Richardson
Aidan P. McKay
Frederik Peschke
Glenn A. Burley
Allan J. B. Watson
Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
Beilstein Journal of Organic Chemistry
chemoselectivity
click chemistry
copper
germanium
triazole
title Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
title_full Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
title_fullStr Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
title_full_unstemmed Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
title_short Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
title_sort germanyl triazoles as a platform for cuaac diversification and chemoselective orthogonal cross coupling
topic chemoselectivity
click chemistry
copper
germanium
triazole
url https://doi.org/10.3762/bjoc.20.265
work_keys_str_mv AT johnmhalfordmcguff germanyltriazolesasaplatformforcuaacdiversificationandchemoselectiveorthogonalcrosscoupling
AT thomasmrichardson germanyltriazolesasaplatformforcuaacdiversificationandchemoselectiveorthogonalcrosscoupling
AT aidanpmckay germanyltriazolesasaplatformforcuaacdiversificationandchemoselectiveorthogonalcrosscoupling
AT frederikpeschke germanyltriazolesasaplatformforcuaacdiversificationandchemoselectiveorthogonalcrosscoupling
AT glennaburley germanyltriazolesasaplatformforcuaacdiversificationandchemoselectiveorthogonalcrosscoupling
AT allanjbwatson germanyltriazolesasaplatformforcuaacdiversificationandchemoselectiveorthogonalcrosscoupling