Programmed synthesis of arylthiazoles through sequential C-H couplings

Satoshi Tani, Takahiro N. Uehara, Junichiro Yamaguchi, Kenichiro Itami

Research output: Contribution to journalArticle

138 Citations (Scopus)

Abstract

A programmed synthesis of privileged arylthiazoles via sequential 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.

Original languageEnglish
Pages (from-to)123-135
Number of pages13
JournalChemical Science
Volume5
Issue number1
DOIs
Publication statusPublished - 2014 Jan
Externally publishedYes

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Thiazoles
Palladium
Nickel
Substitution reactions
Catalysts
fatostatin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Programmed synthesis of arylthiazoles through sequential C-H couplings. / Tani, Satoshi; Uehara, Takahiro N.; Yamaguchi, Junichiro; Itami, Kenichiro.

In: Chemical Science, Vol. 5, No. 1, 01.2014, p. 123-135.

Research output: Contribution to journalArticle

Tani, Satoshi ; Uehara, Takahiro N. ; Yamaguchi, Junichiro ; Itami, Kenichiro. / Programmed synthesis of arylthiazoles through sequential C-H couplings. In: Chemical Science. 2014 ; Vol. 5, No. 1. pp. 123-135.
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