Palladium-catalyzed peri -selective chalcogenation of naphthylamines with diaryl disulfides and diselenides via C-H bond cleavage

Masayuki Iwasaki, Wataru Kaneshika, Yuta Tsuchiya, Kiyohiko Nakajima, Yasushi Nishihara

Research output: Contribution to journalArticle

96 Citations (Scopus)

Abstract

A palladium-catalyzed and picolinamide-directed C-H thiolation of naphthylamine derivatives with diaryl disulfides has been developed to provide a convenient route to 8-sulfenyl-1-naphthylamines. The reaction proceeds via a 5-membered palladacycle intermediates to afford the peri-thiolated products exclusively, in contrast to the conventional ortho-functionalization. Moreover, the related direct selenation was also achieved with diaryl diselenides, giving the corresponding selenated products with perfect site-selectivity.

Original languageEnglish
Pages (from-to)11330-11338
Number of pages9
JournalJournal of Organic Chemistry
Volume79
Issue number23
DOIs
Publication statusPublished - Dec 5 2014

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1-Naphthylamine
Palladium
Disulfides
Derivatives
picolinamide

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Palladium-catalyzed peri -selective chalcogenation of naphthylamines with diaryl disulfides and diselenides via C-H bond cleavage. / Iwasaki, Masayuki; Kaneshika, Wataru; Tsuchiya, Yuta; Nakajima, Kiyohiko; Nishihara, Yasushi.

In: Journal of Organic Chemistry, Vol. 79, No. 23, 05.12.2014, p. 11330-11338.

Research output: Contribution to journalArticle

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