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

Research output: Contribution to journalArticle (Academic Journal)peer-review

153 Citations (Scopus)

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

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