Issue 35, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
24 Feb 2018
Accepted
26 Mar 2018
First published
17 Apr 2018
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2018,54, 4398-4401

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, 54, 4398 DOI: 10.1039/C8CC01540F

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