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Atropo‐Enantioselective Oxidation‐Enabled Iridium(III)‐Catalyzed C−H Arylations with Aryl Boronic Esters

Łukasz Woźniak, Nicolai Cramer

2021Angewandte Chemie International Edition44 citationsDOIOpen Access PDF

Abstract

Abstract Atropo‐enantioselective biaryl coupling through C−H bond functionalization is an emerging technology allowing direct construction of axially chiral molecules. This approach is largely limited to electrophilic coupling partners. We report a highly atropo‐enantioselective C−H arylation of tetralone derivatives paired with aryl boronic esters as nucleophilic components. The transformation is catalyzed by chiral cyclopentadienyl (Cp x ) iridium(III) complexes and enabled by oxidatively enhanced reductive elimination from high‐valent cyclometalated Ir‐species.

Topics & Concepts

Enantioselective synthesisIridiumArylElectrophileChemistryCyclopentadienyl complexNucleophileCombinatorial chemistryReductive eliminationCatalysisMedicinal chemistryOrganic chemistryAlkylAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacologyMolecular spectroscopy and chirality
Atropo‐Enantioselective Oxidation‐Enabled Iridium(III)‐Catalyzed C−H Arylations with Aryl Boronic Esters | Litcius