Palladium-Catalyzed Synthesis of Δ(2)-Isoxazoline from Toluene Derivatives Enabled by the Triple Role of Silver Nitrate

Chengliang Li; Hongmei Deng; Chunju Li; Xueshun Jia; Jian Li

doi:10.1021/acs.orglett.5b03059

Palladium-Catalyzed Synthesis of Δ(2)-Isoxazoline from Toluene Derivatives Enabled by the Triple Role of Silver Nitrate

Org Lett. 2015 Nov 20;17(22):5718-21. doi: 10.1021/acs.orglett.5b03059. Epub 2015 Nov 10.

Authors

Chengliang Li^{1

2}, Hongmei Deng³, Chunju Li¹, Xueshun Jia¹, Jian Li¹

Affiliations

¹ Department of Chemistry, Innovative Drug Research Center, Shanghai University , 99 Shangda Road, Shanghai 200444, P. R. China.
² College of Environmental and Chemical Engineering, Shanghai University , Shanghai 200444, P. R. China.
³ Laboratory for Microstructures, Shanghai University , Shanghai, 200444, P. R. China.

PMID: 26555344
DOI: 10.1021/acs.orglett.5b03059

Abstract

A palladium-catalyzed direct synthesis of Δ(2)-isoxazoline from toluene derivatives has been established. The present reaction proceeds through nondirected Csp(3)-H activation, benzylic nitration, dehydration, and cycloaddition. This protocol also features the unusual triple role of silver nitrate in a one-pot reaction.

Publication types

Research Support, Non-U.S. Gov't