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)

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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.