Immobilized Eosin Y for the photocatalytic oxidation of tetrahydroisoquinolines in flow

• Fabian Herbrik^a,b
• Sergio Rossi^a
• Miguel Sanz^b
• Alessandra Puglisi^a
• Maurizio Benaglia^a

• ^aDipartimento di Chimica, Università degli Studi di Milano, Via Camillo Golgi 19, 20133 Milano, Italy
• ^bTaros Chemicals GmbH & Co. KG, Emil-Figge-Strasse 76A, 44227 Dortmund, Germany

A new easy-to-synthesize solid supported Eosin Y and its application in the building of a catalytic continuous flow reactor is reported. The fluidic device was employed to perform tertiary amines in-flow photooxidations followed by a nucleophile addition, with overall productivity increased by one order magnitude. When using the iminium-ions in situ generated or in a telescoped fashion, the resulting Mannich-products were isolated with high diastereoselectivity and up to 90% enantioselectivity, simply using air as terminal oxidant.

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