Programmed synthesis of arylthiazoles through sequential C–H couplings

A programmed synthesis of privileged arylthiazoles viasequential C-H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2,4-diaryl, 2,5-diaryl, 4,5-diaryl, and 2,4,5-t...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2014-01, Vol.5 (1), p.123-135
Main Authors: Tani, Satoshi, Uehara, Takahiro N, Yamaguchi, Junichiro, Itami, Kenichiro
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Couplings
Inhibitors
Nickel
Palladium
Platforms
Synthesis
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Summary:A programmed synthesis of privileged arylthiazoles viasequential C-H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2,4-diaryl, 2,5-diaryl, 4,5-diaryl, and 2,4,5-triaryl) from an unfunctionalized thiazole platform by 11 distinct synthetic routes. We have generated over 150 arylthiazoles by using this methodology. We have applied this method to the rapid synthesis of fatostatin (SREBP inhibitor), and the gram-scale synthesis of triarylthiazoles has been demonstrated.
ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc52199k