Tris(4-azidophenyl)methanol - a novel and multifunctional thiol protecting group

Xujun Qiu; Julian Brückel; Christoph Zippel; Martin Nieger; Frank Biedermann; Stefan Bräse

doi:10.1039/d2ra05997e

Tris(4-azidophenyl)methanol - a novel and multifunctional thiol protecting group

RSC Adv. 2023 Jan 17;13(4):2483-2486. doi: 10.1039/d2ra05997e. eCollection 2023 Jan 11.

Authors

Xujun Qiu¹, Julian Brückel¹, Christoph Zippel¹, Martin Nieger², Frank Biedermann³, Stefan Bräse^{1

4}

Affiliations

¹ Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT) Fritz-Haber-Weg 6 76131 Karlsruhe Germany braese@kit.edu (+49)-721-6084-2903.
² Department of Chemistry, University of Helsinki P. O. Box 55 (A. I. Virtasen aukio 1) 00014 Finland.
³ Karlsruhe Institute of Technology (KIT), Institute of Nanotechnology (INT) Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen Germany.
⁴ Institute of Biological and Chemical Systems - Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology (KIT) Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen Germany.

Abstract

The novel tris(4-azidophenyl)methanol, a multifunctionalisable aryl azide, is reported. The aryl azide can be used as a protecting group for thiols in peptoid synthesis and can be cleaved under mild reaction conditions via a Staudinger reduction. Moreover, the easily accessible aryl azide can be functionalised via copper-catalysed cycloaddition reactions, providing additional opportunities for materials chemistry applications.