Direct ortho-acetoxylation of anilides via palladium-catalyzed sp(2) C-H bond oxidative activation

Guan-Wu Wang; Ting-Ting Yuan; Xue-Liang Wu

doi:10.1021/jo8003088

Direct ortho-acetoxylation of anilides via palladium-catalyzed sp(2) C-H bond oxidative activation

J Org Chem. 2008 Jun 20;73(12):4717-20. doi: 10.1021/jo8003088. Epub 2008 May 17.

Authors

Guan-Wu Wang¹, Ting-Ting Yuan, Xue-Liang Wu

Affiliation

¹ Hefei National Laboratory for Physical Sciences at Microscale, Joint Laboratory of Green Synthetic Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, PR China. gwang@ustc.edu.cn

PMID: 18484772
DOI: 10.1021/jo8003088

Abstract

Various anilides have been directly ortho-acetoxylated through a Pd(OAc)2-catalyzed C-H bond activation process. The amide group in anilides was found to functionalize as an elegant directing group to convert aromatic sp(2) C-H bonds into C-O bonds in high regioselectivity with acetic acid as the acetate source and K(2)S(2)O(8) as the oxidant.