Iridium(I)-catalyzed regioselective C[BOND]H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality

W.J. Kerr, Richard J. Mudd, Laura C. Paterson, John Alexander Brown

Research output: Contribution to journalArticle

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Abstract

Isotopic labelling is a key technology of increasing importance for the investigation of new CH activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed CH activation and hydrogen-isotope exchange at the b-position of unsaturated
organic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3)][PF6] (cod=1,5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective b-activation and labelling of a range of a,b-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.
Original languageEnglish
Pages (from-to)14604-14607
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number45
Early online date5 Oct 2014
DOIs
Publication statusPublished - 3 Nov 2014

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

Keywords

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

Cite this

Kerr, W.J. ; Mudd, Richard J. ; Paterson, Laura C. ; Brown, John Alexander. / Iridium(I)-catalyzed regioselective C[BOND]H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 45. pp. 14604-14607.
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Iridium(I)-catalyzed regioselective C[BOND]H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality. / Kerr, W.J.; Mudd, Richard J.; Paterson, Laura C.; Brown, John Alexander.

In: Chemistry - A European Journal, Vol. 20, No. 45, 03.11.2014, p. 14604-14607.

Research output: Contribution to journalArticle

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AU - Kerr, W.J.

AU - Mudd, Richard J.

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AB - Isotopic labelling is a key technology of increasing importance for the investigation of new CH activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed CH activation and hydrogen-isotope exchange at the b-position of unsaturatedorganic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3)][PF6] (cod=1,5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective b-activation and labelling of a range of a,b-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.

KW - C-H activation

KW - deuterium

KW - hydrogen isotope

KW - iridium

KW - unsaturated compounds

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