3D Multilayer Folding of Chiral and Achiral Targets Cotaining Aryl‐Aryl‐Alkynyl Motifs Enabled by π‐π Stacking

Abstract

3D multi‐layered achiral and chiral compounds containing aryl‐aryl‐alkenyl motifs are considered crucial for achieving planarity via π.π stacking, enhanced stability by conjugation, improved optoelectronic properties and receptor binding capabilities. By taking advantage of palladium (0) catalyzed Suzuki‐Miyaura and Sonogashira cross coupling reactions, newly designed atropisomerically 3D multi‐layered achiral and chiral compounds have been synthesized successfully synthesized that leverage center‐to‐multilayer chirality. These compounds were obtained in overall yields of 27 % to 89 % through flash column chromatography, and comprehensively characterized with their absolute configurations confirmed using X‐ray structural analysis. Utilizing readily available commercial starting materials, fourteen distinct diastereomers with multilayer chirality were successfully synthesized in a seven‐step process, along with fifteen achiral multilayered targets achieved in five steps. This research will open new avenues in the fields of atropisomeric drug designing, bio‐sensing and circularly polarised luminescence materials.