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Updated: Jul 23, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ru(II)/Ru(IV)-catalyzed C(sp2)-H allylation with alkene difunctionalization to access isochroman-1-imines
Ashish Joshi1,2, Shruti Moorthy3, Lilesh Rambhai Chavada1,2
1Fluoro-Agrochemicals Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Tarnaka, Hyderabad, Telangana 500007, India. akpandey@iict.res.in.
Abstract:
Merging C(sp2)-H allylation and alkene difunctionalization events to access isochroman-1-imines, using N-aroyl aminoesters, MBH acetates, and NBS, under Ru(II)/Ru(IV) catalysis has been developed. Using 1H NMR, ESI-MS, HRMS, control reactions, deuterium labeling experiments, and DFT analysis, the allyl transfer (redox) process was proven to involve in C-H allylation rather than olefin insertion. Scale-up and synthetic transformations demonstrated the sustainability of this method.
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