Room Temperature Deoxyfluorination of Benzaldehydes and α-Ketoesters with Sulfuryl Fluoride and Tetramethylammonium Fluoride

Patrick R Melvin; Devin M Ferguson; Sydonie D Schimler; Douglas C Bland; Melanie S Sanford

doi:10.1021/acs.orglett.9b00054

Room Temperature Deoxyfluorination of Benzaldehydes and α-Ketoesters with Sulfuryl Fluoride and Tetramethylammonium Fluoride

Org Lett. 2019 Mar 1;21(5):1350-1353. doi: 10.1021/acs.orglett.9b00054. Epub 2019 Feb 18.

Authors

Patrick R Melvin¹, Devin M Ferguson¹, Sydonie D Schimler¹, Douglas C Bland², Melanie S Sanford¹

Affiliations

¹ Department of Chemistry , University of Michigan , 930 North University Avenue , Ann Arbor , Michigan 48109 , United States.
² CP PD&P Process Chemistry, Corteva Agriscience , Agriculture Division of DowDuPont , 9330 Zionsville Road , Indianapolis , Indiana 46268 , United States.

PMID: 30775926
DOI: 10.1021/acs.orglett.9b00054

Abstract

A method for the room temperature deoxyfluorination of benzaldehydes and α-ketoesters using sulfuryl fluoride and Me₄NF is described. A large scope of aryl and heteroaryl substrates is demonstrated, and this method compares favorably to other common deoxyfluorination methods for many substrates.

Publication types

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