Work

Photocatalyzed C(sp3)–N Bond Activation of Isonitriles for Mizoroki–Heck Cross-Coupling with Vinyl Arenes

Year: 2025

Type: article

Abstract: We report a Mizoroki-Heck reaction enabled by the visible-light-induced Pd-catalyzed C-N bond cleavage of isonitriles. Through a one-carbon activation of amines, we eliminated the need for atom-inefficient activating groups, thereby allowing isonitriles to serve as alkyl radical precursors. The utility of this protocol was demonstrated with a variety of (hetero)aromatic-containing isonitriles and differentially substituted vinyl arenes. This transformation expands the range of cross-coupling reactions that amine precursors can undergo.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c02954

Authors: Allanah B. Wood, Natsuki Mizuno, Sarah Jung, Alexander W. Schuppe

Institution: Vanderbilt University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Vanderbilt University, Chiba University, National Institute of General Medical Sciences