Oxidative biaryl coupling of thiophenes and thiazoles with arylboronic acids through palladium catalysis: Otherwise difficult C4-selective C-H arylation enabled by boronic acids

Sylvia Kirchberg, Satoshi Tani, Kirika Ueda, Junichiro Yamaguchi, Armido Studer, Kenichiro Itami

Research output: Contribution to journalArticle

181 Citations (Scopus)

Abstract

(Chemical Equation Presented) It adds up to 4! Thiophenes and thiazoles can be arylated in the 4- rather than the expected 5-position in a new C-H functionalization reaction (see scheme; TEMPO: 2,2,6,6-tetramethylpiperidine-N- oxyl). The boronic acid proved to be the key to achieving the otherwise difficult C4 selectivity. The method was applied to a concise synthesis of a key pharmacological structure with potential for treatment of Alzheimers disease.

Original languageEnglish
Pages (from-to)2387-2391
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number10
DOIs
Publication statusPublished - 2011 Mar 1
Externally publishedYes

Fingerprint

Boronic Acids
Thiazoles
Thiophenes
Palladium
Thiophene
Catalysis
Acids
2,2,4,4-tetramethylpiperdine-1-oxyl

Keywords

  • Boronic acids
  • C-H arylation
  • Palladium
  • Regioselectivity
  • Thiazoles
  • Thiophenes

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Oxidative biaryl coupling of thiophenes and thiazoles with arylboronic acids through palladium catalysis : Otherwise difficult C4-selective C-H arylation enabled by boronic acids. / Kirchberg, Sylvia; Tani, Satoshi; Ueda, Kirika; Yamaguchi, Junichiro; Studer, Armido; Itami, Kenichiro.

In: Angewandte Chemie - International Edition, Vol. 50, No. 10, 01.03.2011, p. 2387-2391.

Research output: Contribution to journalArticle

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