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

نویسندگان

چکیده

Abstract N-Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with broad range of substituents on both aromatic rings high functional group tolerance. Starting from readily available ortho-brominated aldehydes primary amines, condensation these building blocks under reductive conditions gives N-aryl 2-bromobenzylamines. The C-3/C-4-unit the tetrahydroisoquinoline is introduced using commercially 2-ethoxyvinyl pinacolboronate Suzuki conditions. Finally, crude ortho-ethoxyvinyl benzylamines cyclized an intramolecular amination combination triethylsilane/TFA to give desired N-aryl-1,2,3,4-tetrahydroisoquinolines.

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ژورنال

عنوان ژورنال: Synthesis

سال: 2021

ISSN: ['1791-5155', '1791-5856']

DOI: https://doi.org/10.1055/s-0040-1706002