Iridium(I)-catalyzed Regioselective C-H Activation and Hydrogen Isotope Exchange of Non-aromatic Unsaturated Functionality

William J Kerr, Richard J Mudd, Laura Paterson, Jack Brown

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Isotopic labeling is a key technology of increasing importance for the investigation of new C-H activation and functionalization techniques, as well as in the construction of labeled molecules for use within both organic synthesis and drug discovery. Herein, we report, for the first time, selective iridium-catalyzed C-H activation and hydrogen isotope exchange at the b-position of unsaturated organic compounds. The use of our highly active [Ir[COD](IMes)(PPh3)]PF6 catalyst, under mild reaction conditions, allows the regioselective b-activation and labeling of a range of a,b-unsaturated compounds with differing steric and electronic properties. This novel process delivers high levels of isotope incorporation over short reaction times, using low levels of catalyst loading.
LanguageEnglish
Number of pages5
JournalChemistry - A European Journal
Early online date5 Oct 2014
Publication statusE-pub ahead of print - 5 Oct 2014

Fingerprint

Iridium
Isotopes
Hydrogen
Ion exchange
Chemical activation
Unsaturated compounds
Catalysts
Organic compounds
Labeling
Molecules

Keywords

  • C-H activation
  • iridium
  • hydrogen isotope exchange
  • unsaturated compounds
  • deuterium

Cite this

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abstract = "Isotopic labeling is a key technology of increasing importance for the investigation of new C-H activation and functionalization techniques, as well as in the construction of labeled molecules for use within both organic synthesis and drug discovery. Herein, we report, for the first time, selective iridium-catalyzed C-H activation and hydrogen isotope exchange at the b-position of unsaturated organic compounds. The use of our highly active [Ir[COD](IMes)(PPh3)]PF6 catalyst, under mild reaction conditions, allows the regioselective b-activation and labeling of a range of a,b-unsaturated compounds with differing steric and electronic properties. This novel process delivers high levels of isotope incorporation over short reaction times, using low levels of catalyst loading.",
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Iridium(I)-catalyzed Regioselective C-H Activation and Hydrogen Isotope Exchange of Non-aromatic Unsaturated Functionality. / Kerr, William J; Mudd, Richard J; Paterson, Laura; Brown, Jack.

In: Chemistry - A European Journal, 05.10.2014.

Research output: Contribution to journalArticle

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AU - Mudd, Richard J

AU - Paterson, Laura

AU - Brown, Jack

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KW - deuterium

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