Electrooxidative Allene Annulations by Mild Cobalt-Catalyzed C–H Activation

Versatile cobalt catalysis enabled electrochemical C–H activation with allenes. Thus, allene annulations were accomplished in terms of C–H/N–H functionalizations with excellent levels of chemoselectivity, site selectivity, and regioselectivity under exceedingly mild conditions. Detailed mechanistic...

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Bibliographic Details
Published in:ACS catalysis 2018-10, Vol.8 (10), p.9140-9147
Main Authors: Meyer, Tjark H, Oliveira, João C. A, Sau, Samaresh Chandra, Ang, Nate W. J, Ackermann, Lutz
Format: Article
Language:English
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Summary:Versatile cobalt catalysis enabled electrochemical C–H activation with allenes. Thus, allene annulations were accomplished in terms of C–H/N–H functionalizations with excellent levels of chemoselectivity, site selectivity, and regioselectivity under exceedingly mild conditions. Detailed mechanistic studies were conducted, including reactions with isotopically labeled compounds, kinetic investigations, and in-operando infrared spectroscopic studies. Further, computational studies were supportive of a non-rate-determining C–H cleavage and gave key insights into the regioselectivity of the allene annulation. The practical utility of the user-friendly approach was furthermore highlighted by gram-scale electrocatalysis.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b03066