841-46-3Relevant articles and documents
Zinc-catalyzed transformation of diarylphosphoryl azides to diarylphosphate esters and amides
Ying, Jun,Gao, Qian,Wu, Xiao-Feng
, p. 1540 - 1543 (2020/04/15)
We have developed a facile and efficient procedure for the synthesis of diarylphosphate esters and amides. Using Zn(acac)2 as the catalyst, the reaction of diarylphosphoryl azides with aliphatic alcohols and phenols through an unusual P?N bond cleavage provided a number of diarylphosphate esters in good yields (22 examples, up to 94%). Additionally, various diarylphosphate amides were obtained from the corresponding amines in excellent yields as well (8 examples, up to 96%).
Copper catalyzed synthesis of aryl/alkyl mixed phosphates from diphenylphosphoryl azides and aliphatic alcohols under mild conditions
Jiao, Lin-Yu,Zhang, Ze,Yin, Xiao-Mei,Li, Zhuo,Ma, Xiao-Xun
, p. 39 - 45 (2019/10/03)
An efficient and convenient one-pot protocol is developed to prepare aryl/alkyl mixed phosphates in the presence of copper catalyst under exceptionally mild conditions. A series of versatile, ubiquitous, and inexpensive phosphoryl azides and aliphatic alcohols are combined for the first time ever. Diphenylphosphoryl azide is employed as novel phosphors reagent through an unexpected cleavage of P[sbnd]N bond. The transformation is advantageous with respect to a broad of functional group compatibility and different esterification products are isolated in good to excellent results. This new catalytic system represents a superior platform towards a mild, operationally simple, practical, and scalability alternative to access target molecules. Furthermore, a plausible mechanism is proposed based on insightful mechanistic studies.
Reactive intermediates in the H-phosphonate synthesis of oligonucleotides
Powles, Nicholas,Atherton, John,Page, Michael I.
experimental part, p. 5940 - 5947 (2012/08/28)
The formation of H-phosphonate diesters is an important step in the synthesis of oligonucleotides. Using diphenylchlorophosphate as the activator for the coupling step is often accompanied by side reactions as a result of self 'capping' and other reactions of the reactive intermediate. In the absence of base, the activation of ethyl H-phosphonate with diphenylchlorophosphate probably occurs through the intermediate formation of bis diethyl pyro-di-H-phosphonate rather than the expected diphenyl ethyl pyro-H-phosphonate. Pyridine acts as a nucleophilic catalyst converting diphenylchlorophosphate to its pyridinium adduct. Several side and unwanted reactions are quantified so that conditions to minimise these can be identified.