Metal- and Acid-Free C-H Formylation of Nitrogen Heterocycles: Using Trioxane as an Aldehyde Equivalent Enabled by an Organic-Soluble Oxidant

Org Lett. 2018 Sep 21;20(18):5752-5756. doi: 10.1021/acs.orglett.8b02453. Epub 2018 Sep 6.

Abstract

A metal-free, innate, and practical C-H formylation of nitrogen heterocycles using trioxane as a formyl equivalent is reported. This reaction provides a mild and robust method for modifying medicinally relevant heterocycles with an aldehyde handle. The use of an organic soluble oxidant, tetrabutylammonium persulfate, is critical in promoting the desired coupling.

Publication types

  • Research Support, Non-U.S. Gov't