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

journal contribution
posted on 2023-06-08, 19:29 authored by Joe W Wrigglesworth, Brian Cox, Guy C Lloyd-Jones, Kevin I Booker-Milburn
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.

History

Publication status

  • Published

Journal

Organic Letters

ISSN

1523-7060

Publisher

American Chemical Society

Issue

19

Volume

13

Page range

5326-5329

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2015-01-12

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