Issue 18, 2021

B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines

Abstract

A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines.

Graphical abstract: B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines

Supplementary files

Article information

Article type
Communication
Submitted
20 fev 2021
Accepted
13 abr 2021
First published
13 abr 2021

Org. Biomol. Chem., 2021,19, 4032-4036

B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines

R. Wu and K. Gao, Org. Biomol. Chem., 2021, 19, 4032 DOI: 10.1039/D1OB00316J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements