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Negishi coupling reactions with [11C]CH3I: a versatile method for efficient 11C–C bond formation

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Abstract

Herein, we present a fast, efficient and general one-pot method for the synthesis of 11C-labelled compounds via the Negishi cross-coupling reaction. Our approach, based on the in situ formation of [11C]CH3ZnI and subsequent reaction with aryl halides or triflates, has proven efficient to synthesize [11C]thymidine, a biologically relevant compound with potential applications as a proliferation marker. Theoretical calculations have shown irreversible formation of a tetracoordinated nucleophilic 11C–Zn(II) reagent and electronic requirements for an efficient Negishi coupling.

Graphical abstract: Negishi coupling reactions with [11C]CH3I: a versatile method for efficient 11C–C bond formation

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Publication details

The article was received on 24 Feb 2018, accepted on 26 Mar 2018 and first published on 17 Apr 2018


Article type: Communication
DOI: 10.1039/C8CC01540F
Citation: Chem. Commun., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Negishi coupling reactions with [11C]CH3I: a versatile method for efficient 11C–C bond formation

    L. Rejc, V. Gómez-Vallejo, J. Alcázar, N. Alonso, J. I. Andrés, A. Arrieta, F. P. Cossío and J. Llop, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC01540F

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