Communication

User-Friendly Methylation of Aryl and Vinyl Halides and Pseudohalides with DABAL-Me3

  1. Thea Cooper1,
  2. Andrew Novak1,
  3. Luke D. Humphreys2,
  4. Matthew D. Walker2,
  5. Simon Woodward1

Article first published online: 5 APR 2006

DOI: 10.1002/adsc.200505405

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 348, Issue 6, pages 686–690, April 2006

Additional Information

How to Cite

Cooper, T., Novak, A., Humphreys, L., Walker, M. and Woodward, S. (2006), User-Friendly Methylation of Aryl and Vinyl Halides and Pseudohalides with DABAL-Me3. Advanced Synthesis & Catalysis, 348: 686–690. doi: 10.1002/adsc.200505405

Author Information

  1. 1

    School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK, Fax: (+44)-155-951-3564

  2. 2

    GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK, Fax: (+44)-143-876-4869

Publication History

  1. Issue published online: 5 APR 2006
  2. Article first published online: 5 APR 2006
  3. Manuscript Accepted: 14 FEB 2006
  4. Manuscript Received: 14 OCT 2005

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Keywords:

  • alkylation;
  • aluminium;
  • aryl halides;
  • cross-coupling;
  • palladium;
  • vinyl halides

Graphical Abstract

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Abstract

An extremely technically simple cross-methylation of aryl and vinyl halides and pseudohalides using an air-stable adduct of trimethylaluminium with a Pd(0) catalyst supported by commercially available biarylphosphines gives excellent yields of methylated products (mainly >95%). Reactions can be run with either 0.5 mol % catalyst or without requiring the exclusion of atmospheric oxygen or the drying of solvents in some cases. A wide variety of functional groups is tolerated including CN, OH, CO2R, CHO and NO2.

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