A Site-Specific Synthetic Route to Substituted Inda(box) Ligands
Kimberly A Alley1, Aidan J Clarkson1, Ayaka Uehara1
1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
Abstract:
Aminoindanol-derived bis(oxazoline) ligands are widely used in metal-catalyzed transformations, but the synthesis of structural derivatives is challenging. We report the gram-scale, seven-step synthesis of five bromine-functionalized inda(box) ligands that have varied bridge substituents. The bromoinda(box) ligands undergo late-stage modification via Pd-catalyzed cross-couplings, which allows for the synthesis of twelve unique inda(box) ligands. This complementary synthetic route could enable the discovery of new asymmetric metal-catalyzed transformations through the modification of the inda(box) ligand architecture.
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diazonium Group Substitution: –OH and –H
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition


