Raines Phosphine for Conversion of Azides to Diazo Compounds

By: Dr. Mark Redlich, Chemfiles Volume 10 Number 1

Due to difficulties with their preparation, especially when sensitive functional groups are present, diazo compounds are often overlooked in synthesis despite their synthetic versatility. Raines and Myers have developed a mild method to convert an azido group in the presence of delicate functional groups using a phosphine reagent, resulting in a diazo compound (Scheme 5).1 Formally, this reaction is a reductive fragmentation of the azide, like the venerable Staudinger reaction and is highly selective in most chemical environments.

Scheme 5: azide reaction scheme

Scheme 5: (715069)

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  1. Myers, E. L Raines, R. T. Angew. Chem. Int., Ed. 2009, 48, 2359.

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