Unknown

Dataset Information

0

Merging Regiodivergent Catalysis with Atom-Economical Radical Arylation.

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.

SUBMITTER: Muhlhaus F 

PROVIDER: S-EPMC6852184 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Merging Regiodivergent Catalysis with Atom-Economical Radical Arylation.

Mühlhaus Felix F   Weißbarth Hendrik H   Dahmen Tobias T   Schnakenburg Gregor G   Gansäuer Andreas A  

Angewandte Chemie (International ed. in English) 20190828 40

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<sub>5</sub> H<sub>4</sub> R)<sub>2</sub> TiX<sub>2</sub> catalyst and the inorganic ligand X (X=Cl, OTs). The overall  ...[more]

Similar Datasets

Unknown Integrated catalysis opens new arylation pathways via regiodivergent enzymatic C-H activation.
| S-EPMC4906404 | biostudies-literature
Unknown Ketyl radical reactivity via atom transfer catalysis.
| S-EPMC6504239 | biostudies-literature
Unknown Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.
| S-EPMC4526169 | biostudies-literature
Unknown Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis.
| S-EPMC5915308 | biostudies-literature
Unknown Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct ?-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.
| S-EPMC6448405 | biostudies-literature
Unknown Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium-arene complexes.
| S-EPMC3002019 | biostudies-literature
Unknown Enzyme-controlled nitrogen-atom transfer enables regiodivergent C-H amination.
| S-EPMC4227740 | biostudies-literature
Unknown Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.
| S-EPMC3740597 | biostudies-literature
Unknown Regio- and chemoselective Csp<sup>3</sup>-H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis.
| S-EPMC6244453 | biostudies-literature
Unknown Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.
| S-EPMC4569064 | biostudies-literature