New Heteroannulation Reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H Activation

Joe W. Wrigglesworth, Brian Cox, Guy C. Lloyd-Jones*, Kevin I. Booker-Milburn

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from Al-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O(2), leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality.

Original languageEnglish
Pages (from-to)5326-5329
Number of pages4
JournalOrganic letters
Volume13
Issue number19
DOIs
Publication statusPublished - 7 Oct 2011

Keywords

  • BOND ACTIVATION
  • ROOM-TEMPERATURE
  • REACTIVITY
  • ALKENES
  • SP(2)
  • ACIDS
  • CARBONYLATION
  • ALKALOIDS
  • OXIDANT
  • ARYL

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