Issue 24, 2013
From the journal:

RSC Advances

Pd0-mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid esters: efficient method for incorporation of positron-emitting 11C radionuclide into organic frameworks by coupling between two sp3-hybridized carbons†‡

Hiroko Koyama,a   Zhouen Zhang,b   Ryosuke Ijuin,b   Siqin,a   Jeongwan Son,a   Yuma Hatta,a   Masashi Ohta,a   Masahiro Wakao,a   Takamitsu Hosoya,a   Hisashi Doib  and  Masaaki Suzuki§*b  

* Corresponding authors

a Division of Regeneration and Advanced Medical Science, Graduated School of Medicine, Gifu University, 1-1 Yanagido, Gifu, 501-1194, Japan

b Center for Molecular Imaging Science, RIKEN, 6-7-3 Minatojima–minamimachi, Chuo-ku, Kobe, Hyogo, 650-0047, Japan

Abstract

Pd0-mediated rapid cross coupling between sp3-hybridized carbons of CH3I and benzyl- or cinnamylboronic acid esters using [Pd{P(tert-C4H9)3}2]/CsF in DMF/H2O gave the corresponding methylated compounds in high yield. The utility was well demonstrated for the synthesis of short-lived PET tracer, N-(4-[11C]ethylphenyl)propionamide, in 90 ± 1% radio-HPLC analytical yield and 49 ± 3% radiochemical yield.

Graphical abstract: Pd0-mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid esters: efficient method for incorporation of positron-emitting 11C radionuclide into organic frameworks by coupling between two sp3-hybridized carbons

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Article information

DOI
https://doi.org/10.1039/C3RA40815A
Article type
Paper
Submitted
18 Feb 2013
Accepted
28 Mar 2013
First published
13 May 2013

RSC Adv., 2013,3, 9391-9401

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Pd0-mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid esters: efficient method for incorporation of positron-emitting 11C radionuclide into organic frameworks by coupling between two sp3-hybridized carbons

H. Koyama, Z. Zhang, R. Ijuin, Siqin, J. Son, Y. Hatta, M. Ohta, M. Wakao, T. Hosoya, H. Doi and M. Suzuki, RSC Adv., 2013, 3, 9391 DOI: 10.1039/C3RA40815A

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