Development of a simple system for the oxidation of electron-rich diazo compounds to ketones. Issue 8 (24th February 2016)

• Record Type: Journal Article
• Authors: O'Connor, Nicholas R.; Bolgar, Peter; Stoltz, Brian M.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 8(2016)
• Page Start: 849
• Page End: 851
• Publication Date: 2016-02-24
• Subjects: Oxidation -- Diazo compounds -- Ketones -- Dimethyl sulfoxide -- Chemoselective transformation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.01.020
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Mild heating of diazo compounds in DMSO furnishes ketone products in moderate to excellent yields. The reaction is particularly effective on electron-rich substrates and exhibits high chemoselectivity, allowing for the use of diazo compounds containing additional oxidation-prone functional groups. This straightforward protocol offers an alternate route to synthetically useful α-ketoesters from readily available aryl diazoacetates.