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

Merging C(sp(2))-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 H-1 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.

Automated summary

A method for accessing isochroman-1-imines by merging C(sp(2))-H allylation and alkene difunctionalization events using N-aroyl aminoesters, MBH acetates, and NBS under Ru(ii)/Ru(iv) catalysis has been developed. The involvement of allyl transfer (redox) process in C-H allylation rather than olefin insertion was proven through H-1 NMR, ESI-MS, HRMS, control reactions, deuterium labeling experiments, and DFT analysis. Scale-up and synthetic transformations demonstrated the sustainability of this method.