Issue 40, 2016
From the journal:

Chemical Communications

Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C–H activation of unprotected tetrazoles†

William J. Kerr,*a   David M. Lindsay,a   Marc Reid,a   Jens Atzrodt,b   Volker Derdau,b   Patrick Rojahnb  and  Remo Weckb  

* Corresponding authors

a Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland, UK
E-mail: w.kerr@strath.ac.uk

b DSAR, DD-ICMS, Sanofi-Aventis Deutschland GmbH, Industriepark Höchst, G876, 65926 Frankfurt, Germany

Abstract

The first examples of selective ortho-directed C–H activation with unprotected 2-aryltetrazoles are described. A new base-assisted protocol for iridium(I) hydrogen isotope exchange catalysis allows access to ortho-deuterated and tritiated tetrazoles, including the tetrazole-containing pharmaceutical, Valsartan. Preliminary mechanistic studies are also presented.

Graphical abstract: Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C–H activation of unprotected tetrazoles

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Article information

DOI
https://doi.org/10.1039/C6CC02137A
Article type
Communication
Submitted
10 Mar 2016
Accepted
20 Apr 2016
First published
20 Apr 2016

Chem. Commun., 2016,52, 6669-6672

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Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C–H activation of unprotected tetrazoles

W. J. Kerr, D. M. Lindsay, M. Reid, J. Atzrodt, V. Derdau, P. Rojahn and R. Weck, Chem. Commun., 2016, 52, 6669 DOI: 10.1039/C6CC02137A

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