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Quinone-mediated hydrogen anode for non-aqueous reductive electrosynthesis
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Journal Article
Quinone-mediated hydrogen anode for non-aqueous reductive electrosynthesis
2023
Overview
Electrochemical synthesis can provide more sustainable routes to industrial chemicals
1
–
3
. Electrosynthetic oxidations may often be performed ‘reagent-free’, generating hydrogen (H
2
) derived from the substrate as the sole by-product at the counter electrode. Electrosynthetic reductions, however, require an external source of electrons. Sacrificial metal anodes are commonly used for small-scale applications
4
, but more sustainable options are needed at larger scale. Anodic water oxidation is an especially appealing option
1
,
5
,
6
, but many reductions require anhydrous, air-free reaction conditions. In such cases, H
2
represents an ideal alternative, motivating the growing interest in the electrochemical hydrogen oxidation reaction (HOR) under non-aqueous conditions
7
–
12
. Here we report a mediated H
2
anode that achieves indirect electrochemical oxidation of H
2
by pairing thermal catalytic hydrogenation of an anthraquinone mediator with electrochemical oxidation of the anthrahydroquinone. This quinone-mediated H
2
anode is used to support nickel-catalysed cross-electrophile coupling (XEC), a reaction class gaining widespread adoption in the pharmaceutical industry
13
–
15
. Initial validation of this method in small-scale batch reactions is followed by adaptation to a recirculating flow reactor that enables hectogram-scale synthesis of a pharmaceutical intermediate. The mediated H
2
anode technology disclosed here offers a general strategy to support H
2
-driven electrosynthetic reductions.
A quinone-mediated hydrogen anode design shows that hydrogen can be used as the electron source in non-aqueous reductive electrosynthesis, for a more sustainable way to make molecules at larger scale.
Publisher
Nature Publishing Group UK,Nature Publishing Group
Subject
