Modular design

Physics

Monomer

Organic chemistry

Combinatorial chemistry

Palladium

Stereochemistry

Operating system

Gas compressor

Enantioselective synthesis

Catalysis

Axial compressor

Axial chirality

Atropisomer

Chemistry

Norbornene

Alkyl

Computer science

Aryl

Polymer

Thermodynamics

Journal of the American Chemical Society

Herein, we report a modular and convergent strategy for the assembly of atropisomeric o-terphenyls with 1,2-diaxes via palladium/chiral norbornene cooperative catalysis and axial-to-axial diastereoinduction. Readily available aryl iodides, 2,6-substituted aryl bromides, and potassium aryl trifluoroborates are used as the building blocks, laying the foundation for diversity-oriented synthesis of these scaffolds (46 examples). Other features include the unique axial-to-axial diastereoinduction mode, construction of two axes in a single operation, and step economy. DFT calculations are performed to rationalize the axial-to-axial diastereoinduction process. Synthetic utilities of this method in preparation of atropisomeric oligophenyls, chiral catalysts, and ligands are demonstrated.

Catalytic Synthesis of Atropisomeric <i>o</i>-Terphenyls with 1,2-Diaxes via Axial-to-Axial Diastereoinduction

Catalytic Synthesis of Atropisomeric o-Terphenyls with 1,2-Diaxes via Axial-to-Axial Diastereoinduction