Visible-Light-Induced Copper-Catalyzed Radical Reactions of Diazo Arylidene Succinimides to Access the Pyromellitic Diimide (PMDI) Core

The synthesis of pyromellitic diimides (PMDIs) through visible-light-promoted copper-catalyzed reaction of diazo arylidene succinimides has been accomplished without the use of external oxidants. This transformation involves a carbon radical from diazo arylidene succinimides with a copper catalyst o...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2024-11, Vol.26 (48), p.10241-10247
Main Authors: Meher, Kajal B., Laha, Debasish, Dharpure, Pankaj D., Bhat, Ramakrishna G.
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The synthesis of pyromellitic diimides (PMDIs) through visible-light-promoted copper-catalyzed reaction of diazo arylidene succinimides has been accomplished without the use of external oxidants. This transformation involves a carbon radical from diazo arylidene succinimides with a copper catalyst or photocatalyst via the proton-coupled electron transfer (PCET) process. This approach successfully challenges a long-standing paradigm in the synthesis of PMDIs. Notably, copper complex (CuNCS) formed in situ proved to be playing a pivotal role to drive the reaction via photoinitiation. Additionally, we synthesized a PMDI molecule known for its prominent aggregation-induced emission (AIE) property. For the very first time, we have synthesized unsymmetrical PMDIs by employing the developed protocol.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03604