New heteroannulation reactions of n-alkoxybenzamides by Pd(II) catalyzed C–H activation

Wrigglesworth, Joe W, Cox, Brian, Lloyd-Jones, Guy C and Booker-Milburn, Kevin I (2011) New heteroannulation reactions of n-alkoxybenzamides by Pd(II) catalyzed C–H activation. Organic Letters, 13 (19). pp. 5326-5329. ISSN 1523-7060

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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 O2, 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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Tom Gittoes
Date Deposited: 12 Jan 2015 14:25
Last Modified: 12 Jan 2015 14:25
URI: http://sro.sussex.ac.uk/id/eprint/52046
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