A C-H activation-based enantioselective synthesis of lower carbo[n]helicenes

Guo, Shu-Min and Huh, Soohee and Coehlo, Max and Shen, Li and Pieters, Grégory and Baudoin, Olivier. (2023) A C-H activation-based enantioselective synthesis of lower carbo[n]helicenes. Nature chemistry, 15. pp. 872-880.

[img] PDF - Published Version
Available under License CC BY (Attribution).


Official URL: https://edoc.unibas.ch/94917/

Downloads: Statistics Overview


The three-dimensional structure of carbohelicenes has fascinated generations of molecular chemists and has been exploited in a wide range of applications. Their strong circularly polarized luminescence has attracted considerable attention in recent years due to promising applications in new optical materials. Although the enantioselective synthesis of fused carbo- and heterohelicenes has been achieved, a direct catalytic enantioselective method allowing the synthesis of lower, non-fused carbo[n]helicenes (n = 4-6) is still lacking. We report here that Pd-catalysed enantioselective C-H arylation in the presence of a unique bifunctional phosphine-carboxylate ligand provides a simple and general access to these lower carbo[n]helicenes. Computational mechanistic studies indicate that both the C-H activation and reductive elimination steps contribute to the overall enantioselectivity. The observed enantio-induction seems to arise from a combination of non-covalent interactions and steric repulsion between the substrate and ligand during the two key reductive elimination steps. The photophysical and chiroptical properties of the synthesized scalemic [n]helicenes have been systematically studied.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Nature Research
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
edoc DOI:
Last Modified:08 Jun 2023 14:13
Deposited On:08 Jun 2023 14:13

Repository Staff Only: item control page