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Ir-Catalyzed Asymmetric Hydroarylation of Alkynes for the Synthesis of Axially Chiral Heterobiaryls

Pablo Vázquez-Domínguez, Antonio Romero‐Arenas, Rosario Fernández, José M. Lassaletta, Abel Ros

2022ACS Catalysis30 citationsDOIOpen Access PDF

Abstract

The catalytic hydroarylation of alkynes has emerged as an excellent methodology for the synthesis of functionalized alkenes with excellent levels of regio- and stereocontrol (syn). However, in spite of the great progress in this field, the number of asymmetric methodologies is still scarce. Herein, we report an atroposelective Ir-catalyzed C–H hydroarylation of alkynes, which enables the asymmetric synthesis of axially chiral heterobiaryl trisubstituted olefins in good to high yields and enantioselectivities up to 98% ee.

Topics & Concepts

CatalysisEnantioselective synthesisChemistryCombinatorial chemistryAxial symmetryAxial chiralityOrganic chemistryPhysicsQuantum mechanicsAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology
Ir-Catalyzed Asymmetric Hydroarylation of Alkynes for the Synthesis of Axially Chiral Heterobiaryls | Litcius