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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Non-directed Pd-catalysed electrooxidative olefination of arenes
Subir Panja1, Salman Ahsan2, Tanay Pal1
1IIT Bombay, Department of Chemistry and IDP, Climate Studies Powai Mumbai 400076 India dmaiti@iitb.ac.in arnabdutta@chem.iitb.ac.in.
Abstract:
The Fujiwara-Moritani reaction is a powerful tool for the olefination of arenes by Pd-catalysed C-H activation. However, the need for superstoichiometric amounts of toxic chemical oxidants makes the reaction unattractive from an environmental and atom-economical view. Herein, we report the first non-directed and regioselective olefination of simple arenes via an electrooxidative Fujiwara-Moritani reaction. The versatility of this operator-friendly approach was demonstrated by a broad substrate scope which includes arenes, heteroarenes and a variety of olefins. Electroanalytical studies suggest the involvement of a Pd(ii)/Pd(iv) catalytic cycle via a Pd(iii) intermediate.
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