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

Beilstein J Org Chem. 2024 Dec 5:20:3198-3204. doi: 10.3762/bjoc.20.265. eCollection 2024.

Authors

John M Halford-McGuff¹, Thomas M Richardson¹, Aidan P McKay¹, Frederik Peschke², Glenn A Burley², Allan J B Watson¹

Affiliations

¹ EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.
² Department of Pure & Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.

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.

Grants and 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.