2021-01-07
Carina Glas, Ricky Wirawan, Franz Bracher
N-Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with a broad range of substituents on both aromatic rings and high functional group tolerance. Starting from readily available ortho-brominated aromatic aldehydes and primary aromatic amines, condensation of these building blocks under reductive conditions gives N-aryl 2-bromobenzylamines. The C-3/C-4-unit of the tetrahydroisoquinoline is introduced using commercially available 2-ethoxyvinyl pinacolboronate under Suzuki conditions. Finally, the obtained crude ortho-ethoxyvinyl benzylamines are cyclized via an intramolecular reductive amination using the combination of triethylsilane/TFA to give the desired N-aryl-1,2,3,4-tetrahydroisoquinolines.
Speaker: Prof. Dr. Thomas Carell
Ludwig-Maximilians-Universität München
Department of Chemistry Butenandtstr. 5 - 13
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Institute for Chemical Epigenetics Munich (ICEM)
Ludwig-Maximilians-Universität München
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Prof. Dr. Hendrik Zipse (Spokesman)
LMU Munich
Department of Chemistry
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LMU Munich
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LMU Munich
Department of Chemistry
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