Regioselective One-Step Synthesis of 4-Fluoroalkylated Isoquinolines via Carbopalladation Reaction of Fluorine-Containing Alkynes

The palladium-catalyzed annulation reaction of fluoroalkylated alkynes with various 2-iodobenzylidenamines was investigated. In the presence of a catalytic amount of Pd(PPh3)4, the reaction took place smoothly to give the corresponding 4-fluoroalkylated isoquinoline in high yield as a single isomer....

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 70; no. 24; pp. 10172 - 10174
Main Authors:	Konno, Tsutomu, Chae, Jungha, Miyabe, Tomotsugu, Ishihara, Takashi
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 25-11-2005
Subjects:	Alkynes - chemistry Chemistry Exact sciences and technology Fluorine - chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Isoquinolines - chemical synthesis Isoquinolines - chemistry Molecular Structure Organic chemistry Preparations and properties Stereoisomerism Catalytic reaction Transition element complexes Isoquinoline derivatives Acetylenic compound Regioselectivity Nitrogen heterocycle Palladium complex Annelation Organic iodine compounds Organic fluorine compounds Benzenic compound Platinoid Complexes Chemical synthesis Alkyne
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Summary:	The palladium-catalyzed annulation reaction of fluoroalkylated alkynes with various 2-iodobenzylidenamines was investigated. In the presence of a catalytic amount of Pd(PPh3)4, the reaction took place smoothly to give the corresponding 4-fluoroalkylated isoquinoline in high yield as a single isomer. No other regioisomer was detected.
Bibliography:	istex:5F4D20E6C942C35097220F2B8227E977F2B10EA9 ark:/67375/TPS-GXHW8VTS-R ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo051700v