PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES

B BURNS, R GRIGG, [No Value] SANTHAKUMAR, Seshadri SRIDHARAN, P STEVENSON, T WORAKUN

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Abstract

A new, wide ranging, synthetically powerful, catalytic tandem cyclisation-anion capture process is proposed which depends on the rate of cyclisation of an organopalladium specifies (RPdX) onto a proximate alkene or diene being significantly faster than anion exchange and reductive elimination in the sequence RPdX --> RPdY --> RY + Pd(0). The catalytic cyclisation - anion capture sequence is illustrated for hydride capture by a wide variety of substrates giving rise to fused- and spiro-, carbo- and hetero-cyclic systems, regio- and stereo-specifically.

Original languageEnglish
Pages (from-to)7297-7320
Number of pages24
JournalTetrahedron
Volume48
Issue number35
Publication statusPublished - 28 Aug 1992

Keywords

  • PALLADIUM
  • CATALYSIS
  • CYCLIZATION
  • HYDRIDE CAPTURE
  • TANDEM PROCESS
  • METAL-PROMOTED CYCLIZATION
  • 5-EXO-TRIG-VERSUS 6-ENDO-TRIG CYCLIZATIONS
  • STEREOSELECTIVE TOTAL SYNTHESIS
  • INTRAMOLECULAR HECK REACTIONS
  • BIS-EXOCYCLIC DIENES
  • POLYENE CYCLIZATIONS
  • CRYSTAL-STRUCTURE
  • CARBON CENTERS
  • SILVER-NITRATE
  • RING-SYSTEMS

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