Merging Regiodivergent Catalysis with Atom-Economical Radical Arylation

Angewandte Chemie
Felix MühlhausAndreas Gansäuer

Abstract

A titanocene-catalyzed regiodivergent radical arylation is described that allows access to either enantiomerically pure tetrahydroquinolines or indolines from a common starting material. The regioselectivity of epoxide opening that results in the high selectivity of heterocycle formation is controlled by two factors, the absolute configuration of the enantiopure ligands of the (C5 H4 R)2 TiX2 catalyst and the inorganic ligand X (X=Cl, OTs). The overall reaction is atom-economical and constitutes a radical Friedel-Crafts alkylation.

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Citations

Mar 28, 2020·Angewandte Chemie·Andreas GansäuerRobert A Flowers
Aug 28, 2020·Chemical Society Reviews·Manfred Manßen, Laurel L Schafer
Feb 5, 2021·Chemistry : a European Journal·Christoph KernJan Streuff
Oct 28, 2019·The Journal of Organic Chemistry·Terry McCallumSong Lin
Nov 23, 2021·Journal of the American Chemical Society·Minghui ZhouBas de Bruin
Oct 26, 2021·Chemistry : a European Journal·Mojtaba Hajiloo ShayeganXin Cui

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