Iron-catalyzed C(sp2)-H and C(sp3)-H arylation by triazole assistance

Qing Gu, Hamad H. Al Mamari, Karolina Graczyk, Emelyne Diers, Lutz Ackermann

Research output: Contribution to journalArticle

185 Citations (Scopus)

Abstract

Modular 1,2,3-triazoles enabled iron-catalyzed C-H arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp 2)-H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp3)-H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted C-H activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries. With a little help: A versatile iron catalyst allows the arylation of C(sp2)-H and C(sp3)-H bonds in the presence of a modular and removable triazolyldimethylmethyl (TAM) auxiliary, whose structure can be varied through 1,3-dipolar azide-alkyne cycloadditions.

Original languageEnglish
Pages (from-to)3868-3871
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number15
DOIs
Publication statusPublished - Apr 7 2014

Keywords

  • C-H activation
  • chelation
  • iron
  • ruthenium
  • triazoles

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

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