Palladium/Norbornene Cooperative Catalysis 2-Fold C–H/C–X Coupling: Construction of Polycyclic Aromatic Hydrocarbons from Brominated Benzimidazoles

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

A palladium/norbornene (NBE)-catalyzed 2-fold C-H/C-X coupling reaction of aryl iodides is reported. Bromine-substituted benzimidazoles were chosen as electrophilic and termination reagents, the versatile polycyclic aromatic hydrocarbon products successfully obtained. The strategy overcomes challenge catalyst poisoning by heterocyclic substrates. In addition, imidazole moiety in product endowed with a localization role, thus enabling compounds to be applied wider synthetic scenario, fluorescence persisted. Furthermore, bioactivity evaluation has identified three promising leading 3b, 4e, 4i.

Language: Английский

Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: March 19, 2025

Tetracoordinate boron-based fluorescent materials have shown extensively applications in chemistry, biology and science owing to their unique optoelectronic properties. However, constructing chiral boron-stereogenic fluorophores through practical universal strategies remains rare challenging. Herein, as a proof of concept, we report an enantioselective postfunctionalization boron dipyrromethene dyes (BODIPYs), acess BODIPYs moderate good yields with commendable enantioselectivity. Chiral attracted increasing attention not only distinctively photophysical properties circularly polarized luminescence (CPL) materials, but also diversely structural modification. In this·work, present phase-transfer-catalyst enabled C–N coupling reaction diverse nucleophiles. This method serves SNAr (nucleophilic aromatic substitution reaction) route achieve series amido/amino well demonstrates promising CD and·CPL·activities, excellent biocompatibility, high specificities, showing potential imaging agents. Constructing Here, the authors

Language: Английский

Organocatalyzed Enantioselective C–N Bond-Forming S_NAr Reactions for Synthesizing Stereogenic-at-Boron BODIPYs

JACS Au, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

Language: Английский