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

William J. Kerr, David M. Lindsay, Marc Reid, Jens Atzrodt, Volker Derdau, Patrick Rojahn, Remo Weck

Research output: Contribution to journalArticle

24 Citations (Scopus)

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.
LanguageEnglish
Pages6669-6672
Number of pages4
JournalChemical Communications
Volume52
Issue number40
Early online date20 Apr 2016
DOIs
Publication statusE-pub ahead of print - 20 Apr 2016

Fingerprint

Valsartan
Tetrazoles
Iridium
Isotopes
Drug products
Catalysis
Hydrogen
Ion exchange
Chemical activation
Pharmaceutical Preparations
1H-tetrazole

Keywords

  • iridium (I) hydrogen isotope exchange catalysis
  • ortho-directed C-H activation
  • 2-aryltetrazoles

Cite this

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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.",
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Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions : C-H activation of unprotected tetrazoles. / Kerr, William J.; Lindsay, David M.; Reid, Marc; Atzrodt, Jens; Derdau, Volker; Rojahn, Patrick; Weck, Remo.

In: Chemical Communications, Vol. 52, No. 40, 20.04.2016, p. 6669-6672.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions

T2 - Chemical Communications

AU - Kerr, William J.

AU - Lindsay, David M.

AU - Reid, Marc

AU - Atzrodt, Jens

AU - Derdau, Volker

AU - Rojahn, Patrick

AU - Weck, Remo

PY - 2016/4/20

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AB - 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.

KW - iridium (I) hydrogen isotope exchange catalysis

KW - ortho-directed C-H activation

KW - 2-aryltetrazoles

U2 - 10.1039/C6CC02137A

DO - 10.1039/C6CC02137A

M3 - Article

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