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; Zhouen Zhang; Ryosuke Ijuin; Siqin; Jeongwan Son; Yuma Hatta; Masashi Ohta; Masahiro Wakao; Takamitsu Hosoya; Hisashi Doi; Masaaki Suzuki

doi:10.1039/C3RA40815A

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 Doi^b and Masaaki Suzuki §*^b

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^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.

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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†‡

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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

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