Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: a general protocol potentially useful for the synthesis of short-lived 11CH3-labeled PET tracers with a 1-propynyl group

Takamitsu Hosoya; Masahiro Wakao; Yurie Kondo; Hisashi Doi; Masaaki Suzuki

doi:10.1039/B311532A

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Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: a general protocol potentially useful for the synthesis of short-lived ¹¹CH₃-labeled PET tracers with a 1-propynyl group†

Takamitsu Hosoya,^ab Masahiro Wakao,^a Yurie Kondo,^b Hisashi Doi^a and Masaaki Suzuki*^ab

Author affiliations

* Corresponding authors

^a Division of Regeneration and Advanced Medical Science, Gifu University Graduate School of Medicine, Yanagido 1-1, Gifu 501-1193, Japan
E-mail: suzukims@biomol.gifu-u.ac.jp

^b Department of Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan

Abstract

The Pd(0)-mediated rapid coupling (trapping) reaction of methyl iodide with an excess amount of alkynyltributylstannane has been developed with the aim to incorporate a short-lived ¹¹C-labeled methyl group into biologically active organic compounds with a 1-propynyl structural unit.

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Supplementary files

General experimental remarks and synthetic methods and characterization of tributylalkynylstannanes and the corresponding methylacetylenes DOC (171K)

Article information

DOI: https://doi.org/10.1039/B311532A
Article type: Communication
Submitted: 22 Sep 2003
Accepted: 30 Oct 2003
First published: 11 Nov 2003

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Org. Biomol. Chem., 2004,2, 24-27

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Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: a general protocol potentially useful for the synthesis of short-lived ¹¹CH₃-labeled PET tracers with a 1-propynyl group

T. Hosoya, M. Wakao, Y. Kondo, H. Doi and M. Suzuki, Org. Biomol. Chem., 2004, 2, 24 DOI: 10.1039/B311532A

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Organic & Biomolecular Chemistry