628708-20-3Relevant academic research and scientific papers
Mechanistic investigation of the Staudinger ligation
Lin, Fiona L.,Hoyt, Helen M.,Van Halbeek, Herman,Bergman, Robert G.,Bertozzi, Carolyn R.
, p. 2686 - 2695 (2007/10/03)
The Staudinger ligation of azides and phosphines has found widespread use in the field of chemical biology, but the mechanism of the transformation has not been characterized in detail. In this work, we undertook a mechanistic study of the Staudinger liga
Conversion of Aryl Azides to O-Alkyl Imidates via Modified Staudinger Ligation
Restituyo, Jose A.,Comstock, Lindsay R.,Petersen, Scott G.,Stringfellow, Thomas,Rajski, Scott R.
, p. 4357 - 4360 (2007/10/03)
(Equation presented) o-Carboalkoxy triarylphosphines are shown to react with aryl azides to provide Staudinger ligation products bearing O-alkyl imidate linkages. This is in contrast to alkyl azides whose ligation to o-carboalkoxy triarylphosphines has been reported to yield amide-linked materials. This extension of the Staudinger ligation for coupling of abiotic reagents under biocompatible conditions highlights the utility of commercially available triarylphosphines through which suitable linkers can be attached via an ester moiety.
