Issue 33, 2010
From the journal:

Chemical Communications

A mild deuterium exchange reaction of free carboxylic acids by photochemical decarboxylation†

Tatsuya Itou,*a   Yasuharu Yoshimi,*b   Keisuke Nishikawa,b   Toshio Morita,b   Yutaka Okada,a   Nobuyuki Ichinosec  and  Minoru Hatanakad  

* Corresponding authors

a Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, 1-1-1 Noji-Higashi, Kusatsu 525-8577, Japan
E-mail: t-itou@fc.ritsumei.ac.jp
Tel: +81 77-561-2810

b Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui 910-8507, Japan

c Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, Japan

d Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan

Abstract

Deuterium exchange of a carboxy group was achieved by photochemical decarboxylation of free carboxylic acids in the presence of thiol and a small amount of D2O, and a deuterated product with excellent deuterium content was obtained; this reaction is a practical means of synthesizing regioselective deuterium-labelled compounds under mild reaction conditions.

Graphical abstract: A mild deuterium exchange reaction of free carboxylic acids by photochemical decarboxylation

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Article information

DOI
https://doi.org/10.1039/C0CC01464H
Article type
Communication
Submitted
18 May 2010
Accepted
01 Jul 2010
First published
26 Jul 2010

Chem. Commun., 2010,46, 6177-6179

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A mild deuterium exchange reaction of free carboxylic acids by photochemical decarboxylation

T. Itou, Y. Yoshimi, K. Nishikawa, T. Morita, Y. Okada, N. Ichinose and M. Hatanaka, Chem. Commun., 2010, 46, 6177 DOI: 10.1039/C0CC01464H

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