Issue 3, 2023

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

Abstract

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 via the merger of photocatalysis and electrochemistry. CeCl3 and Cu/BOX were used as co-catalysts to promote the decarboxylation and cyanation, and both catalysts were regenerated via anodic oxidation. This method establishes a proof of concept enantioselective transformation via photoelectrocatalysis. Studies by DFT calculations provided mechanistic insight on enantioselectivity control.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
29 Sept. 2022
Accepted
06 Dec. 2022
First published
07 Dec. 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 705-710

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

Y. Yuan, J. Yang and J. Zhang, Chem. Sci., 2023, 14, 705 DOI: 10.1039/D2SC05428K

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