Palladium-catalyzed cross-methylation of haloarenes possessing active hydrogen atoms by intramolecularly stabilized dimethylindium and dimethylaluminum reagents

Nimer Jaber, Dmitri Gelman, Herbert Schumann, Sebastian Dechert, Jochanan Blum*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

While the intramolecularly stabilized aluminum complex [(CH3)2AlOCH2CH2 N(CH3)2]2 (2a) reacts readily with 4-bromophenol to give methane and [(4-BrC6H4O)2Al-OCH2 CH2N(CH3)2]2 (7), the demethylation of the analogous indium complex [(CH3)2InOCH2CH2 N(CH3)2]2 2c is very slow. This inertness of 2c enables it to cross-methylate bromophenols and other bromoarenes with active hydrogen atoms in the presence of soluble palladium phosphane catalysts. The cross-methylation by 2c can be carried out under an ambient atmosphere. The ring-bound bromine atoms in 7 are replaced by CH3 groups when treated with an excess of the methylation reagent 2a, and the resulting aluminum cresolate liberates 4-methylphenol upon hydrolysis.

Original languageAmerican English
Pages (from-to)1628-1632
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number10
DOIs
StatePublished - 2002

Keywords

  • Aluminum
  • Cross coupling
  • Indium
  • N,O ligands

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