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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.

Graphical abstract: Ru(ii)/Ru(iv)-catalyzed C(sp2)–H allylation with alkene difunctionalization to access isochroman-1-imines

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