title: New heteroannulation reactions of N-alkoxybenzamides by Pd(II) catalyzed C-H activation.
abstract: A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from N-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.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Joe W
authors.initials: JW
authors.lastname: Wrigglesworth
authors.forename: Brian
authors.initials: B
authors.lastname: Cox
authors.forename: Guy C
authors.initials: GC
authors.lastname: Lloyd-Jones
authors.forename: Kevin I
authors.initials: KI
authors.lastname: Booker-Milburn
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D001549:Benzamides; D010165:Palladium; D002244:Carbon; D006859:Hydrogen