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One‐Pot Synthesis of Fluorinated 1‐Benzoyl‐3,4‐dihydroisoquinolines from [2‐( o ‐Alkynylphenyl)ethyl]amines by a Hydroamination/Oxidation Sequence
Author(s) -
Severin René,
Reimer Jessica,
Doye Sven
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901034
Subject(s) - hydroamination , chemistry , intramolecular force , alkyne , catalysis , combinatorial chemistry , organic chemistry , side chain , ring (chemistry) , polymer chemistry , medicinal chemistry , polymer
Fluorinated 1‐benzoyl‐3,4‐dihydroisoquinolines can easily be synthesized by a new one‐pot procedure from corresponding fluorinated [2‐( o ‐alkynylphenyl)ethyl]amines in high yields. The one‐pot process consists of an initial [Ind 2 TiMe 2 ]‐catalyzed intramolecular alkyne hydroamination and a subsequent Pd‐catalyzed oxidation of the benzyl side chain of the resulting hydroamination product. The process tolerates electron‐donating and ‐withdrawing substituents on the benzene ring that is converted into the benzoyl side chain of the products as well as ortho ‐substitution.