Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry

The development of an efficient and straightforward method for decarboxylative coupling using common alkyl carboxylic acid is of great value. However, decarboxylative coupling with nucleophiles always needs stoichiometric chemical oxidants or substrate prefunctionalization. Herein, we report a proto...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2023-01, Vol.14 (3), p.705-710
Main Authors: Yuan, Yin, Yang, Junfeng, Zhang, Junliang
Format: Article
Language:English
Subjects:
Anodizing
Carboxylic acids
Catalysts
Coupling
Decarboxylation
Electrochemistry
Enantiomers
Nucleophiles
Oxidation
Oxidizing agents
Photocatalysis
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The development of an efficient and straightforward method for decarboxylative coupling using common alkyl carboxylic acid is of great value. However, decarboxylative coupling with nucleophiles always needs stoichiometric chemical oxidants or substrate prefunctionalization. Herein, we report a protocol for Cu-catalyzed enantioselective decarboxylative cyanation the merger of photocatalysis and electrochemistry. CeCl and Cu/BOX were used as co-catalysts to promote the decarboxylation and cyanation, and both catalysts were regenerated anodic oxidation. This method establishes a proof of concept enantioselective transformation photoelectrocatalysis. Studies by DFT calculations provided mechanistic insight on enantioselectivity control.
ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc05428k