Synthesis of substituted benzoxacycles via a domino ortho-alkylation/Heck coupling sequence

J Org Chem. 2006 Jun 23;71(13):4937-42. doi: 10.1021/jo060552l.

Abstract

The synthesis of a variety of alkylidene benzoxacycles via a domino palladium-catalyzed ortho-alkylation/intramolecular Heck reaction is described. Under the optimized conditions [Pd(OAc)2 (10 mol %), P(2-Furyl)3 (20 mol %), norbornene (4 equiv), Cs2CO3 (2 equiv), CH3CN, 80 degrees C], aryl iodides with oxygen-tethered Heck acceptors are coupled with alkyl bromides (5 equiv) to generate a variety of six- and seven-membered-ring benzoxacyclic products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Benzoxazines / chemical synthesis*
  • Benzoxazines / chemistry
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Benzoxazines
  • Palladium