Exo-Selective Intramolecular C–H Alkylation with 1,1-Disubstituted Alkenes by Rare-Earth Catalysts: Construction of Indanes and Tetralins with an All-Carbon Quaternary Center
Aniket Mishra, Ping Wu, Xuefeng Cong, Masayoshi Nishiura, Gen Luo, Zhaomin Hou
Abstract
We report herein the exo-selective, regiospecific annulation of a wide range of functionalized aromatic substrates with 1,1-disubstituted alkenes through C(sp2)–H and benzylic C(sp3)–H activation by half-sandwich rare-earth catalysts. This protocol offers a straightforward and atom-efficient route for the synthesis of a family of indane and tetralin derivatives bearing an all-carbon quaternary stereocenter that were difficult to access previously by other catalysts. The reaction mechanism has been elucidated by deuterium-labeling experiments and DFT calculations.
Topics & Concepts
IndaneChemistryAnnulationStereocenterCatalysisIntramolecular forceTetralinAlkylationMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis