Sonogashira Coupling of Functionalized Trifloyl Oxazoles and Thiazoles with Terminal Alkynes:  Synthesis of Disubstituted Heterocycles

This paper describes Sonogashira cross-coupling of functionalized 2-, 4-, and 5-trifloyl oxazoles and thiazoles with terminal alkynes. This methodology has been extended to 2,4-ditrifloylthiazoles, which results in regioselective cross-coupling at the C2-position of the thiazole. The resulting 2-alk...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 15; pp. 2485 - 2488
Main Authors Langille, Neil F, Dakin, Les A, Panek, James S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.07.2002
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Chemistry, Pharmaceutical - methods
Heterocyclic Compounds - chemical synthesis
Oxazoles - chemistry
Palladium - chemistry
Physical Sciences
Science & Technology
Thiazoles - chemistry
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Summary:This paper describes Sonogashira cross-coupling of functionalized 2-, 4-, and 5-trifloyl oxazoles and thiazoles with terminal alkynes. This methodology has been extended to 2,4-ditrifloylthiazoles, which results in regioselective cross-coupling at the C2-position of the thiazole. The resulting 2-alkynyl-4-trifloylthiazoles are effective electrophiles in a second palladium(0)-mediated cross-coupling reaction.
Bibliography:Medline
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol026099r