Jump to main content
Jump to site search

Issue 3, 2020
Previous Article Next Article

Reductive coupling of imines with redox-active esters by visible light photoredox organocatalysis

Author affiliations

Abstract

The addition of organometallic compounds to imines is a direct way for accessing α-branched secondary amines which are found in numerous bioactive molecules. Although convenient, such reactions typically involve the formation and isolation of the nucleophile in the case of Grignard reactions, or the in situ formation of the nucleophile for Barbier reactions, leading to stoichiometric amounts of metallic wastes. Herein, we report the direct alkylation of imines with redox-active esters by visible light photoorganocatalysis. With Rose bengal as inexpensive photocatalyst, and green light as sustainable energy source, the synthesis of a wide range of amines and θ-amino esters was achieved from inexpensive feedstock chemicals, in a highly modular fashion.

Graphical abstract: Reductive coupling of imines with redox-active esters by visible light photoredox organocatalysis

Back to tab navigation

Supplementary files

Article information


Submitted
29 Nov 2019
Accepted
13 Jan 2020
First published
22 Jan 2020

Org. Chem. Front., 2020,7, 602-608
Article type
Research Article

Reductive coupling of imines with redox-active esters by visible light photoredox organocatalysis

J. Jia, Q. Lefebvre and M. Rueping, Org. Chem. Front., 2020, 7, 602
DOI: 10.1039/C9QO01428D

Social activity

Search articles by author

Spotlight

Advertisements