Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Copper catalyzed N-formylation of α-silyl-substituted tertiary N-alkylamines by air

Author affiliations

Abstract

A site-selective method to prepare N-formyl amines efficiently that relies on the copper(I)-catalyzed oxidation of α-silyl-substituted tertiary N-alkylamines by air at room temperature is described. The oxidative protocol was shown to exhibit excellent functional group tolerance as it was applicable to a wide variety of amine substrates and a number of bioactive molecules and natural products. Moreover, it delinates a ligand- and additive-free amine oxidation process mediated by a low-cost metal salt with oxygen from air taking on the role of both the terminal oxidant and as part of the formylation reagent, which is unprecedented in copper catalysis. It also offers the first synthetic method that can selectively generate α-amino radical species as reactive intermediates from α-silylamines under non-photochemical reaction conditions.

Graphical abstract: Copper catalyzed N-formylation of α-silyl-substituted tertiary N-alkylamines by air

Back to tab navigation

Supplementary files

Article information


Submitted
08 Apr 2020
Accepted
26 May 2020
First published
27 May 2020

Green Chem., 2020, Advance Article
Article type
Paper

Copper catalyzed N-formylation of α-silyl-substituted tertiary N-alkylamines by air

Y. Zhao, L. D. Bruce, J. Jin, B. Xia and P. W. H. Chan, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC01242D

Social activity

Search articles by author

Spotlight

Advertisements