Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T

Takumi Abe, Hiroyuki Takeda, Yoshihisa Miwa, Koji Yamada, Reiko Yanada, Minoru Ishikura

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N1-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)2 , primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.

Original languageEnglish
Pages (from-to)233-241
Number of pages9
JournalHelvetica Chimica Acta
Volume93
Issue number2
DOIs
Publication statusPublished - Feb 2010
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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