Merging Regiodivergent Catalysis with Atom-Economical Radical Arylation.

Angew Chem Int Ed Engl

Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard Domagk-Straße 1, 53121, Bonn, Germany.

Published: October 2019

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 (C H R) TiX 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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6852184PMC
http://dx.doi.org/10.1002/anie.201908860DOI Listing

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