Conversion of Aryl Azides to O-Alkyl Imidates via Modified Staudinger Ligation
Organic Letters2003Vol. 5(23), pp. 4357–4360
Citations Over TimeTop 10% of 2003 papers
Abstract
[reaction: see text] 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.
Related Papers
- → The Preparation of 2,3-Disubstituted-4-thiazolidones. II. 3-Alkyl (and Aralkyl) 2-Aryl Derivatives(1948)17 cited
- → ChemInform Abstract: REACTION OF ALKYL(ARYL)DICHLOROPHOSPHINES AND N,N,N′,N′‐TETRAALKYL‐P‐PHENYLPHOSPHONOUS DIAMIDES WITH O‐AMINOPHENOL(1977)
- → ChemInform Abstract: Dioxygenyl Hexafluoroantimonate: A Useful Reagent for Preparing Cation Radical Salts in Good Yield.(1987)
- → ChemInform Abstract: Reaction of Secondary Acetylenic Bromides with Sodium Nitrite: Synthesis of 3,5‐Alkyl(Aryl)‐4‐nitroisoxazoles.(1988)
- → ChemInform Abstract: Comparison of Different Reducing Systems in the Synthesis of Functionally Substituted Benzylamines from Alkyl Aryl Ketones and Aromatic Aldehydes.(2010)