Organocatalytic α‐Aminoalkylation of Azomethine Imines by α‐Silylamines under Blue LED Light

A synthetic method to prepare 1,2‐diamines efficiently that relies on the 4CzPN‐catalysed α‐aminoalkylation of azomethine imines by secondary and tertiary α‐silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal‐ and additive‐free reaction conditions at r...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-07, Vol.365 (14), p.2422-2427
Main Authors: Li, Jiacheng, Carli, Lorenzo, Kyne, Sara Helen, Chan, Philip Wai Hong
Format: Article
Language:English
Subjects:
1,2-diamines
azomethine imines
Diamines
Imines
Light emitting diodes
photoredox catalysis
Room temperature
α-aminoalkylation
α-silylamines
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Summary:A synthetic method to prepare 1,2‐diamines efficiently that relies on the 4CzPN‐catalysed α‐aminoalkylation of azomethine imines by secondary and tertiary α‐silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal‐ and additive‐free reaction conditions at room temperature, the synthetic protocol was shown to afford product yields up to 99% and applicable to the late‐stage functionalisation of three drug molecules and the gramme‐scale preparation of one example.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300463