Direct Conversion of Aldehydes and Ketones into Azides by Sequential Nucleophilic Addition and Substitution

This report describes the direct conversion of aldehydes and ketones into alkyl azides by the addition of common organometallic reagents and tandem conversion of the resulting alkoxides without isolation of the intermediate alcohols. A wide range of aldehydes and organometallic reagents (R-Li or R-MgX) are suitable participants in this process. Additional reaction telescoping beyond azide formation is demonstrated.