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.
Bibliographical noteFunding Information:
We thank Amy Ott for acquiring mass spectra. The American Chemical Society ? Petroleum Research Fund (ACS-PRF) (PRF#56505-DNI1) and the University of Minnesota are thanked for financial support. V. P. S. acknowledges the University of Minnesota ? Undergraduate Research Opportunity (UMN-UROP) for support.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
- Click chemistry
- Green chemistry