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

Kerr, William J. and Lindsay, David and Reid, Marc and Atzrodt, Jens and Derdau, Volker and Rojahn, Patrick and Weck, Remo (2016) Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions : C-H activation of unprotected tetrazoles. Chemical Communications, 52 (40). pp. 6669-6672. ISSN 1359-7345 (https://doi.org/10.1039/C6CC02137A)

[thumbnail of Kerr-etal-CC2016-Iridium-catalysed-ortho-HD-and-HT-exchange-under-basic-conditions]
Preview
Text. Filename: Kerr_etal_CC2016_Iridium_catalysed_ortho_HD_and_HT_exchange_under_basic_conditions.pdf
Accepted Author Manuscript

Download (4MB)| Preview

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.

ORCID iDs

Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Lindsay, David ORCID logoORCID: https://orcid.org/0000-0003-4498-5094, Reid, Marc ORCID logoORCID: https://orcid.org/0000-0003-4394-3132, Atzrodt, Jens, Derdau, Volker, Rojahn, Patrick and Weck, Remo;