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Chiral PSiSi‐Ligand Enabled Iridium‐Catalyzed Atroposelective Intermolecular C−H Silylation

Bo Yang, Jihui Gao, Xing-Fa Tan, Yicong Ge, Chuan He

2023Angewandte Chemie International Edition60 citationsDOIOpen Access PDF

Abstract

Catalytic enantioselective intermolecular C-H silylation offers an efficient approach for the rapid construction of chiral organosilicon compounds, but remains a significant challenge. Herein, a new type of chiral silyl ligand is developed, which enables the first iridium-catalyzed atroposelective intermolecular C-H silylation reaction of 2-arylisoquinolines. This protocol features mild reaction conditions, high atom economy, and remarkable yield with excellent stereoselectivity (up to 99 % yield, 99 % ee), delivering enantioenriched axially chiral silane platform molecules with facile convertibility. Key to the success of this unprecedented transformation relies on a novel chiral PSiSi-ligand, which facilitates the intermolecular C-H silylation process with perfect chem-, regio- and stereo-control via a multi-coordinated silyl iridium complex.

Topics & Concepts

SilylationIridiumChemistryOrganosiliconLigand (biochemistry)Enantioselective synthesisIntermolecular forceCatalysisChiral ligandCombinatorial chemistryStereoselectivitySilanesYield (engineering)MoleculeOrganic chemistrySilaneMaterials scienceReceptorMetallurgyBiochemistryAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis