Mechanistic studies on the Pd-catalyzed direct C-H arylation of 2-substituted thiophene derivatives with arylpalladium bipyridyl complexes

Marc Steinmetz, Kirika Ueda, Stefan Grimme*, Junichiro Yamaguchi, Sylvia Kirchberg, Kenichiro Itami, Armido Studer

*この研究の対応する著者

研究成果: Article査読

56 被引用数 (Scopus)

抄録

Direct C-H phenylation of 2-ethylthiophene and 2-chlorothiophene with PhPdI(bipy) complex to form either the corresponding 4-phenyl or 5-phenylthiophene derivative is studied under stoichiometric conditions using various Lewis acids as additives. It is shown that reactions occur via the corresponding cationic Pd complex (PhPdbipy +) and that the counteranion determines the regioselectivity. High-level DFT calculations reveal that C-C bond formation occurs via a carbopalladation pathway and not via electrophilic palladation. These calculations give some indications regarding the regioselectivity of the thiophene arylation.

本文言語English
ページ(範囲)1256-1260
ページ数5
ジャーナルChemistry - An Asian Journal
7
6
DOI
出版ステータスPublished - 2012 6月
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 有機化学

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