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

Ashish Joshi; Shruti Moorthy; Lilesh Rambhai Chavada; Saurabh Kumar Singh; Ashok Kumar Pandey

doi:10.1039/d3cc01604h

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

Chem Commun (Camb). 2023 Aug 1;59(62):9497-9500. doi: 10.1039/d3cc01604h.

Authors

Ashish Joshi^{1

2}, Shruti Moorthy³, Lilesh Rambhai Chavada^{1

2}, Saurabh Kumar Singh³, Ashok Kumar Pandey^{1

2}

Affiliations

¹ Fluoro-Agrochemicals Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Tarnaka, Hyderabad, Telangana 500007, India. akpandey@iict.res.in.
² Chemical Science Division, Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
³ Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502285, India. sksingh@chy.iith.ac.in.

PMID: 37440259
DOI: 10.1039/d3cc01604h

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.