4.7 Article

Ligand-Free Silver(I)-Catalyzed Intramolecular Friedel-Crafts Alkylation of Arenes with Allylic Alcohols

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 3, Pages 319-324

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800628

Keywords

alkylation; aromatic compounds; catalysis; Friedel-Crafts reaction; silver

Funding

  1. M.I.U.R. (Rome)
  2. Fondazione del Monte 1473
  3. University of Bologna
  4. NewChem S.p.A.

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The silver-catalyzed direct activation of allylic alcohols as electrophilic partners for intramolecular Friedel-Crafts alkylation of arenes is described. Use of silver triflate (AgOTf; 10 mol%) enabled functionalized 1-vinyl-1,2,3,4-tetrahydronaphthalenes and a 4-vinyl-1,2,3,4-tetrahydroisoquinoline to be isolated in good yields with high levels of regiochemistry, under a ligand-free regime.

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