A Rapid Approach to the Synthesis of Highly Functionalized Tetrahydroisoquinolines

A palladium-catalyzed domino ortho-alkylation/alkenylation forming up to three new C−C bonds furnishes functionalized tetrahydroisoquinolines in up to 87% yield. Extension to the formation of tetrahydrobenzoazepines and tetrahydroisoquinolinones is presented.

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Bibliographic Details
Published in:Journal of organic chemistry 2009-02, Vol.74 (4), p.1791-1793
Main Authors: Thansandote, Praew, Gouliaras, Christina, Turcotte-Savard, Marc-Olivier, Lautens, Mark
Format: Article
Language:English
Subjects:
Azepines - chemical synthesis
Azepines - chemistry
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics
Organic chemistry
Palladium - chemistry
Preparations and properties
Tetrahydroisoquinolines - chemical synthesis
Tetrahydroisoquinolines - chemistry
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Description
Summary:A palladium-catalyzed domino ortho-alkylation/alkenylation forming up to three new C−C bonds furnishes functionalized tetrahydroisoquinolines in up to 87% yield. Extension to the formation of tetrahydrobenzoazepines and tetrahydroisoquinolinones is presented.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo8025725