One-Pot Synthesis of Fluorinated 1-Benzoyl-3,4-dihydroisoquinolines from [2-(o-Alkynylphenyl)ethyl]amines by a Hydroamination/Oxidation Sequence

被引:5
作者
Severin, Rene [1 ]
Reimer, Jessica [1 ]
Doye, Sven [1 ]
机构
[1] Carl von Ossietzky Univ Oldenburg, Inst Reine & Angew Chem, D-26111 Oldenburg, Germany
关键词
Antitumor agents; Nitrogen heterocycles; Hydroarmination; Palladium; Oxidation; Titanium; CATALYZED INTERMOLECULAR HYDROAMINATION; ASYMMETRIC HYDROAMINATION; INTRAMOLECULAR HYDROAMINATION; ALKENES; COMPLEXES;
D O I
10.1002/ejoc.200901034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:51 / 54
页数:4
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