66910-79-0Relevant academic research and scientific papers
B(C6F5)3 as a highly effective catalyst for the phosphoryl transfer reaction
Xue, Weihua,Zhang, Lifen
, p. 1797 - 1800 (2012/10/29)
The phosphoryl transfer reactions of diphenyl chlorophosphate with a wide range of alcohols were catalyzed by tris(pentafluorophenyl)boron [B(C 6F5)3], giving the corresponding phosphate esters in excellent yields. This me
Substitution- and elimination-free phosphorylation of functionalized alcohols catalyzed by oxidomolybdenum tetrachloride
Liu, Cheng-Yuan,Pawar, Vijay D.,Kao, Jun-Qi,Chen, Chien-Tien
experimental part, p. 188 - 194 (2010/07/03)
Among 14 oxidometallic species examined for catalytic phosphorylation of the tested alcohols, oxidomolybdenum tetrachloride (MoOCl4) was found to be the most efficient with a negligible background reaction mediated by triethylamine (Et3N). The new catalytic protocol can be applied to the chemoselective phosphorylations of primary, secondary and tertiary alcohols as well as the substitution-free phosphorylations of allylic, propargylic, and benzylic alcohols. Functionalized alcohols bearing acetonide, tetrahydropyranyl ether, tert-butyldimethylsilyl ether, or ester group are also amenable to the new catalytic protocol. The most difficult scenarios involve substitution-free phosphorylations of 1-phenylethanol and 1-(2-naphthyl)ethanol which can be effected in 95 and 90% yields, respectively. ESI-MS, IR, 1H, and 31P NMR spectroscopic analyses of the reaction progress suggest the intermediacy of an alkoxyoxidomolybdenum trichloride-triethylamine adduct such as [(RO)Mo(O)Cl3-Et3N] to be responsible for the catalytic turnover.
Phosphorylation of alcohols with N-phosphoryl oxazolidinones employing copper(II) triflate catalysis
Jones, Simon,Smanmoo, Chaiwat
, p. 3271 - 3274 (2007/10/03)
(Chemical Equation Presented) Phosphoryl transfer from N-phosphoryl 5,5-diphenyl oxazolidinone is efficiently catalyzed by copper(II) triflate. The utility of this method has been demonstrated in the phosphorylation of representative primary, secondary, tertiary, phenolic, and allylic alcohols. These reaction conditions are significantly milder than employing alkoxides and allow the phosphorylation of biologically relevant molecules.
N-Phosphoryl oxazolidinones as effective phosphorylating agents
Jones, Simon,Smanmoo, Chaiwat
, p. 1585 - 1588 (2007/10/03)
A number of N-phosphoryl oxazolidinones have been prepared and evaluated, the best being 5,5-diphenyl oxazolidinones, the utility of which was demonstrated in the phosphorylation of a number of representative primary, secondary, tertiary, and phenolic alcohols.
An improved method for Lewis acid catalyzed phosphoryl transfer with Ti(t-BuO)4
Jones, Simon,Selitsianos, Dimitrios,Thompson, Kate J.,Toms, Steven M.
, p. 5211 - 5216 (2007/10/03)
Several inorganic esters have been evaluated as phosphoryl transfer catalysts. Of these, Ti(t-BuO)4 was found to be the most effective catalyst giving excellent yields of the desired phosphate esters. The loading of the catalyst could be reduced to a little as 5 mol % for a majority of substrates with no loss in the yield of product. This methodology is significantly more versatile than using TiCl4 and is suitable for the phosphorylation of more complex carbohydrates and molecules of biological interest.
A simple, general and improved procedure for phosphorylation of alcohols catalyzed by indium(III) chloride
Ranu, Brindaban C.,Das, Arijit
, p. 1063 - 1064 (2007/10/03)
A general and efficient procedure has been developed for the preparation of dialkyl phosphate esters by indium(III) chloride catalyzed phosphoryl transfer from diethyl and diphenyl chlorophosphate to a variety of alcohols and phenols in THF in presence of triethylamine.
A simple and effective method for phosphoryl transfer using TiCl4 catalysis
Jones, Simon,Selitsianos, Dimitrios
, p. 3671 - 3673 (2007/10/03)
(graph presented) A number of Lewis acids have been evaluated as catalysts for the phosphoryl transfer, the most efficient being TiCl4. Application of this methodology to the phosphorylation of a number of representative target alcohols is presented.
3-Phosphono-2-(N-cyanoimino)thiazolidine derivatives, new phosphorylating agents for alcohols
Maezaki, Naoyoshi,Furusawa, Akemi,Hirose, Yuki,Uchida, Shuji,Tanaka, Tetsuaki
, p. 3493 - 3498 (2007/10/03)
We have developed new phosphorylating agents, 3-phosphono-2-(N-cyanoimino)-thiazolidine derivatives (3-phosphono-NCTs), which were readily synthesized by phosphorylation of NCT, and transformed primary and secondary alcohols into phosphates in good yield. The transfer of three kinds of dialkylphosphono groups [(PhO)2P(O)-, (EtO)2P(O)-, (Cl3CCH2O)2P(O)-] proceeded in excellent yields. Selective phosphorylation of various alcohols was also accomplished.
