Catalytic methylation of C-H bonds using CO2 and H2

Yuehui Li, Tao Yan, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

104 Scopus citations

Abstract

Formation of C-C bonds from CO2 is a much sought after reaction in organic synthesis. To date, other than C-H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C-C bond formation. In fact, to the best of our knowledge no catalytic methylation of C-H bonds using CO2 and H2 has been reported. Described herein is the combination of CO2 and H2 for efficient methylation of carbon nucleophiles such as indoles, pyrroles, and electron-rich arenes. Comparison experiments which employ paraformaldehyde show similar reactivity for the CO2/H2 system. Capturing: Carbon dioxide in the presence of H2 is shown to be an efficient methylating reagent for carbon nucleophiles such as 2-substituted indoles, pyrroles, and electron-rich arenes. Experimental data support the formal capture of formaldehyde. acac=acetylacetonate, triphos=1,1,1-tris(diphenylphosphinomethyl)ethane.

Original languageEnglish
Pages (from-to)10476-10480
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume53
Issue number39
DOIs
StatePublished - 14 Jul 2014
Externally publishedYes

Keywords

  • C-H activation
  • carbon dioxide
  • heterocycles
  • hydrogen
  • ruthenium

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