Triazole-assisted ruthenium-catalyzed C-H arylation of aromatic amides

Hamad H. Al Mamari, Emelyne Diers, Lutz Ackermann

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Site-selective ruthenium(II)-catalyzed direct arylation of amides was achieved through C-H cleavages with modular auxiliaries, derived from easily accessible 1,2,3-triazoles. The triazolyldimethylmethyl (TAM) bidentate directing group was prepared in a highly modular fashion through copper(I)-catalyzed 1,3-dipolar cycloaddition and allowed for ruthenium-catalyzed C-H arylations on arenes and heteroarenes, as well as alkenes, by using easy-to-handle aryl bromides as the arylating reagents. The triazole-assisted C-H activation strategy was found to be widely applicable, to occur under mild reaction conditions, and the catalytic system was tolerant of important electrophilic functionalities. Notably, the flexible triazole-based auxiliary proved to be a more potent directing group for the optimized ruthenium(II)-catalyzed direct arylations, compared with pyridyl-substituted amides or substrates derived from 8-aminoquinoline. Assisting activation: Ruthenium(II)-catalyzed C-H arylations of (hetero)arenes and alkenes have been achieved with aryl halides through removable bidentate auxiliaries derived from modular 1,2,3-triazoles (see scheme; TAM=triazolyldimethylmethyl).

Original languageEnglish
Pages (from-to)9739-9743
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number31
DOIs
Publication statusPublished - Jul 28 2014

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Triazoles
Ruthenium
Amides
Alkenes
Olefins
Chemical activation
Cycloaddition
Bromides
Copper
Substrates

Keywords

  • amides
  • aryl halides
  • C-H activation
  • catalysis
  • ruthenium
  • triazoles

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Triazole-assisted ruthenium-catalyzed C-H arylation of aromatic amides. / Al Mamari, Hamad H.; Diers, Emelyne; Ackermann, Lutz.

In: Chemistry - A European Journal, Vol. 20, No. 31, 28.07.2014, p. 9739-9743.

Research output: Contribution to journalArticle

Al Mamari, Hamad H. ; Diers, Emelyne ; Ackermann, Lutz. / Triazole-assisted ruthenium-catalyzed C-H arylation of aromatic amides. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 31. pp. 9739-9743.
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