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 Feb 2021
Accepted
13 Apr 2021
First published
13 Apr 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

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