Issue 31, 2018

Platinum(iv) azido complexes undergo copper-free click reactions with alkynes


We report our investigations into the first examples of copper-free 1,3-dipolar cycloaddition (click) reactions of electrophiles with a PtIV azido complex. The Pt-IV azido complex trans, trans, trans-[PtIV(py)2(N3)2(OH)2] (1) was reactive towards dimethyl acetylenedicarboxylate (DMAD) (2), diethyl acetylenedicarboxylate DEACD (3), N-[(1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane (BCN) (11) and dibenzocyclooctyne-amine (DBCO) (12) resulting in formation of the corresponding mono (a) and bis-substituted (b) complexes. Complexes of 2 undergo further reactions between the Pt centre and the carbonyl group to form 2a′ and 2b′. This is not seen for the products of the corresponding PtII azido complex trans-[Pt(py)2(N3)2] with acetylene 2. Novel complexes 2a′, 2b′, 11a and 11b have been characterised by multinuclear NMR, IR and UV-vis spectroscopy and ESI-MS. These reactions represent new synthetic routes to novel Pt(IV) complexes.

Graphical abstract: Platinum(iv) azido complexes undergo copper-free click reactions with alkynes

Supplementary files

Article information

Article type
06 Nov 2017
05 Jan 2018
First published
26 Feb 2018
This article is Open Access
Creative Commons BY license

Dalton Trans., 2018,47, 10553-10560

Platinum(IV) azido complexes undergo copper-free click reactions with alkynes

N. J. Farrer, G. Sharma, R. Sayers, E. Shaili and P. J. Sadler, Dalton Trans., 2018, 47, 10553 DOI: 10.1039/C7DT04183G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity