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

Tools

Kerr, W.J. and Mudd, Richard J. and Paterson, Laura C. and Brown, John Alexander (2014) Iridium(I)-catalyzed regioselective C[BOND]H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality. Chemistry - A European Journal, 20 (45). pp. 14604-14607. ISSN 1521-3765 (https://doi.org/10.1002/chem.201405114)

[thumbnail of Kerr-etal-CAEJ-2014-Iridium-I-catalyzed-regioselective-C-H-Activation]
Preview
 PDF. Filename: Kerr_etal_CAEJ_2014_Iridium_I_catalyzed_regioselective_C_H_Activation.pdf
Accepted Author Manuscript
Download (768kB)| Preview

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.

ORCID iDs

Kerr, W.J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Mudd, Richard J. ORCID logoORCID: https://orcid.org/0000-0001-5786-3745, Paterson, Laura C. and Brown, John Alexander;
  • Item type:Article
    ID code:50429
    Dates:
    Date
    Event
    3 November 2014
    Published
    5 October 2014
    Published Online
    4 September 2014
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:19 Nov 2014 10:00
    Last modified:28 Nov 2024 01:10
    URI:https://strathprints.strath.ac.uk/id/eprint/50429
CORE (COnnecting REpositories)