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Published February 24, 2016 | Supplemental Material
Journal Article Open

Development of a simple system for the oxidation of electron-rich diazo compounds to ketones


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 ɑ-ketoesters from readily available aryl diazoacetates.

Additional Information

© 2016 Elsevier Ltd. Received 7 December 2015, Revised 5 January 2016, Accepted 6 January 2016, Available online 8 January 2016. The authors wish to thank the NSF (CHE-1265591), Amgen, and Caltech for financial support. P.B. is grateful to St Catharine's College (University of Cambridge) and the Haller US Travel Fund for their support of an undergraduate summer research exchange program. Dr. David VanderVelde (NMR), Dr. Mona Shahgholi (HRMS), and Shoshana Bachman (ATR-IR) are thanked for assistance with characterization.

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