Work

Reductant-Free NiF 2 /Picolinic Acid-Catalyzed Coupling–Cyclization of 2-Iodobenzamides with Malonates

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A ligand-enabled NiF 2 /picolinic acid catalyst system enabled an efficient and chemoselective coupling–cyclization of ortho -halo benzamides, including ortho -iodo- and ortho -bromobenzamides, with malonates or 1,3-diketoesters to furnish homophthalimides under operationally simple conditions. The reaction proceeded with high selectivity for the activation of benzamide-proximal aryl halide (C–I or C–Br) while tolerating additional aryl C–Br functionality at other positions, which remained intact throughout the transformation. Broad functional-group tolerance was observed across both benzamide and nucleophile classes, delivering the desired products in consistently high yields. Control experiments were consistent with the involvement of a redox-assisted nickel catalytic cycle. This cost-effective strategy provided a general and practical approach for constructing homophthalimide frameworks from readily accessible substrates.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.6c00528

Authors: Gunniga Tanomsiri, Jun Takaoka, Jumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat

Institutions: Chulabhorn Graduate Institute, Ministry of Higher Education, Science, Research and Innovation, Chiba University, Chulabhorn Research Institute

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Ministry of Education, Chulabhorn Research Institute, Thailand Science Research and Innovation, Chulabhorn Graduate Institute, Chulabhorn Royal Academy