Work

Atroposelective Synthesis of Azobenzenes by Palladium-Catalyzed Cross-Coupling of Racemic Biaryl Triflates and Diazenyl Pronucleophiles

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A kinetic resolution of racemic biaryl monotriflates by an atroposelective palladium-catalyzed diazenylation enables the synthesis of azobenzene derivatives decorated with an axially chiral substituent. The C(sp 2 )–N(sp 2 ) cross-coupling reaction makes use of silylated diazenes as diazenyl anion equivalents, and chiral ferrocene-based bisphosphine ligands act as effective supporting ligands. The resulting chiral azobenzenes bearing binaphthyl and naphthyl/phenyl backbones undergo reversible trans – cis isomerization under irradiation with LEDs of different wavelengths, highlighting their potential use in photoresponsive chiroptical materials.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c09097

Authors: Kezhuo Zhang, Martin Oestreich

Institution: Technische Universität Berlin

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Deutscher Akademischer Austauschdienst, China Scholarship Council, Einstein Stiftung Berlin, Technische Universität Berlin