Electroreduction of unactivated alkenes using water as hydrogen source

Herein, we report an electroreduction of unactivated alkyl alkenes enabled by [Fe]-H, which is provided through the combination of anodic iron salts and the silane generated in situ via cathodic reduction, using H 2 O as an H-source. The catalytic amounts of Si-additive work as an H-carrier from H 2...

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Bibliographic Details
Published in:Nature communications 2024-03, Vol.15 (1), p.2780-2780, Article 2780
Main Authors: Wang, Yanwei, Wang, Qian, Wu, Lei, Jia, Kangping, Wang, Minyan, Qiu, Youai
Format: Article
Language:English
Subjects:
140/131
140/58
639/638/161/886
639/638/403/933
639/638/77/886
Alkenes
Chemical reduction
Deuteration
Electrochemistry
Electrowinning
Functional groups
Humanities and Social Sciences
Hydrogenation
Iron
multidisciplinary
Organic chemistry
Pharmaceutical industry
Science
Science (multidisciplinary)
Silanes
Silicon
Substrates
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Summary:Herein, we report an electroreduction of unactivated alkyl alkenes enabled by [Fe]-H, which is provided through the combination of anodic iron salts and the silane generated in situ via cathodic reduction, using H 2 O as an H-source. The catalytic amounts of Si-additive work as an H-carrier from H 2 O to generate a highly active silane species in situ under continuous electrochemical conditions. This approach shows a broad substrate scope and good functional group compatibility. In addition to hydrogenation, the use of D 2 O instead of H 2 O provides the desired deuterated products in good yields with excellent D-incorporation (up to >99%). Further late-stage hydrogenation of complex molecules and drug derivatives demonstrate potential application in the pharmaceutical industry. Mechanistic studies are performed and provide support for the proposed mechanistic pathway. The reduction of unactivated alkyl alkenes is a difficult challenge in organic chemistry. Here, the authors present a silicon-mediated electroreduction of alkyl alkenes, using water as a hydrogen source, enabled by [Fe]-H.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-024-47168-w