Synthesis of Substituted Benzenes via Bi(OTf)3-Mediated Intramolecular Carbonyl Allylation of α-Prenyl or α-Geranyl β-Arylketosulfones

Org Lett. 2015 Jun 19;17(12):3142-5. doi: 10.1021/acs.orglett.5b01461. Epub 2015 Jun 11.

Abstract

Intramolecular carbonyl allylation of α-prenyl or α-geranyl β-arylketosulfones 5 in the presence of molecule sieves (MS) affords substituted benzenes 6-7 in moderate to good yields. The facile transformation proceeds by a synthetic sequence starting with the α-prenylation or α-geranylation of 1 and the Bi(OTf)3-mediated annulation of 5 followed by a sequential desulfonative aromatization or then an intramolecular Friedel-Crafts alkylation. A plausible mechanism has been studied and proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Benzene / chemical synthesis*
  • Benzene / chemistry
  • Mesylates / chemistry*
  • Molecular Structure
  • Neoprene / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Mesylates
  • Sulfhydryl Compounds
  • prenyl
  • Bi(OTf)3
  • Neoprene
  • Benzene