Electrochemical Oxidative Halogenation of N-Aryl Alkynamides for the Synthesis of Spiro[4.5]trienones

J Org Chem. 2021 Jan 1;86(1):917-928. doi: 10.1021/acs.joc.0c02429. Epub 2020 Dec 7.

Abstract

We developed a green method for the synthesis of spiro[4.5]trienones through an electrochemical oxidative halocyclization with N-aryl alkynamides. This reaction was conducted under metal-catalyst- and exogenous-oxidant-free conditions at room temperature. Using readily available LiCl, LiBr, and LiI as the halogen source, a variety of dearomative halo-spirocyclization products were obtained in good to excellent yields with a broad scope and functional group tolerance.

Publication types

  • Research Support, Non-U.S. Gov't