Cationic palladium-catalyzed [5 + 2] annulation of 2-acylmethoxyarylboronic acids and allenoates: synthesis of 1-benzoxepine derivatives

Xufen Yu; Xiyan Lu

doi:10.1021/jo200672w

Cationic palladium-catalyzed [5 + 2] annulation of 2-acylmethoxyarylboronic acids and allenoates: synthesis of 1-benzoxepine derivatives

J Org Chem. 2011 Aug 5;76(15):6350-5. doi: 10.1021/jo200672w. Epub 2011 Jul 11.

Authors

Xufen Yu¹, Xiyan Lu

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

PMID: 21744809
DOI: 10.1021/jo200672w

Abstract

The 1-benzoxepine derivatives were synthesized conveniently by cationic palladium-catalyzed [5 + 2] annulation reaction of 2-acylmethoxyarylboronic acids with allenoates in high yields. This annulation involves the intramolecular nucleophilic addition to ketones without the formation of π-allylpalladium species.