Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides

Laurean Ilies, Tatsuaki Matsubara, Saki Ichikawa, Sobi Asako, Eiichi Nakamura

Research output: Contribution to journalArticle

104 Citations (Scopus)

Abstract

Alkenes, arenes, and heteroarenes possessing an 8-quinolylamide group as the directing group are alkylated with primary and secondary alkyl tosylates, mesylate, and halides in the presence of Fe(acac) 3/ diphosphine as a catalyst and ArZnBr as a base. The reaction proceeds stereospeci fically for alkene substrates and takes place without loss of regiochemical integrity of the starting secondary tosylate, but with loss of the stereochemistry of the chiral center.

Original languageEnglish
Pages (from-to)13126-13129
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number38
DOIs
Publication statusPublished - Sep 24 2014

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Mesylates
Alkylation
Alkenes
Olefins
Iron
Stereochemistry
Catalysts
Substrates

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides. / Ilies, Laurean; Matsubara, Tatsuaki; Ichikawa, Saki; Asako, Sobi; Nakamura, Eiichi.

In: Journal of the American Chemical Society, Vol. 136, No. 38, 24.09.2014, p. 13126-13129.

Research output: Contribution to journalArticle

Ilies, Laurean ; Matsubara, Tatsuaki ; Ichikawa, Saki ; Asako, Sobi ; Nakamura, Eiichi. / Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 38. pp. 13126-13129.
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AU - Nakamura, Eiichi

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