Issue 7, 2022

Platinum on carbon-catalysed site-selective H–D exchange reaction of allylic alcohols using alkyl amines as a hydrogen source

Abstract

We developed a platinum on carbon-catalysed deuteration reaction of tert-allylic alcohols using deuterium oxide as a deuterium source. Amylamine was dehydrogenated by platinum on carbon to generate an appropriate amount of hydrogen gas, which efficiently promoted the H–D exchange reaction. Various allylic alcohols were site-selectively deuterated with good to excellent deuterium contents without hydrogenation of the alkene functionality. The obtained deuterium-labelled allylic alcohols were further transformed into various deuterium-labelled building blocks without degradation of the original deuterium content.

Graphical abstract: Platinum on carbon-catalysed site-selective H–D exchange reaction of allylic alcohols using alkyl amines as a hydrogen source

Supplementary files

Article information

Article type
Research Article
Submitted
03 Feb 2022
Accepted
21 Feb 2022
First published
23 Feb 2022

Org. Chem. Front., 2022,9, 1986-1991

Platinum on carbon-catalysed site-selective H–D exchange reaction of allylic alcohols using alkyl amines as a hydrogen source

K. Park, N. Oka, Y. Sawama, T. Ikawa, T. Yamada and H. Sajiki, Org. Chem. Front., 2022, 9, 1986 DOI: 10.1039/D2QO00177B

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