Synthesis of N-Aryl-1,2,3,4-tetrahydroisoquinolines from N-(2-Bromobenzyl)anilines

A Short Approach to N-Aryl-1,2,3,4-tetrahydroisoquinolines from N-(2-Bromobenzyl)anilines via a Reductive Amination/Palladium-Catalyzed Ethoxyvinylation/Reductive N-Alkylation Sequence: C. Glas, R. Wirawan, F. Bracher

Synthesis 2021, 53, DOI: 10.1055/s-0040-1706002


The 1,2,3,4-tetrahydroisoquinoline scaffold is frequently encountered in bioactive compounds, including those of natural origins. Although a variety of methods exist for preparing this structural motif, less common are methods allowing for an efficient synthesis of the N-aryl counterparts. Recently, Professor Franz Bracher and Carina Glas from Ludwig-Maximilians University (Munich, Germany) reported, together with Ricky Wirawan, on a novel approach to N-aryl-1,2,3,4-tetrahydroisoquinolines of pharmaceutical interest. The compounds were obtained from N-(2-bromobenzyl)anilines via a reductive amination/palladium-catalyzed ethoxyvinylation/reductive N-alkylation sequence.


Professor Bracher said: “This new and flexible approach paves the way for systematic investigation of structure–activity relationships in this pharmaceutically relevant chemotype.”

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