16519-26-9Relevant articles and documents
Mechanistic insight into the nickel-catalyzed cross-coupling of aryl phosphates with arylboronic acids: Potassium phosphate is not a spectator base but is involved in the transmetalation step in the Suzuki-Miyaura reaction
Liu, Liu Leo,Zhang, Shuangyan,Chen, Hu,Lv, Ye,Zhu, Jun,Zhao, Yufen
, p. 2592 - 2595 (2013)
Spectator or actor? Density functional theory calculations were performed to examine the role of the base in the nickel-catalyzed cross-coupling of aryl phosphates with arylboronic acids. Potassium phosphate was found to not act as a spectator base but was involved in the transmetalation step, as shown by a lower barrier than that of a base-free process, owing to the activation of the carbon-boron bond by the base. Further experimental observations support the theoretical findings. Copyright
Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates
Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, p. 5342 - 5347 (2021/06/30)
A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.
Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate
Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
supporting information, p. 4938 - 4941 (2018/08/24)
A metal-, toxic chloride reagent-free activating strategy of various phosphates has been developed. This method enables the facile synthesis of functional phosphates such as alkyl phosphates, aza phosphates, thiophosphate, and mixed diaryl phosphates. A transient phosphorylpyridin-1-ium species in situ generated from phosphates with Tf2O/pyridine readily undergoes a substitution reaction with diverse nucleophiles to form versatile phosphate compounds.
New benzotriazole-based reagents for the phosphonylation of various N-, O-, and S-nucleophiles
Panmand, Deepak S.,Tiwari, Anand D.,Panda, Siva S.,Monbaliu, Jean-Christophe M.,Beagle, Lucas K.,Asiri, Abdullah M.,Stevens, Christian V.,Steel, Peter J.,Hall, C. Dennis,Katritzky, Alan R.
supporting information, p. 5898 - 5901 (2015/01/08)
Benzotriazole surrogates showing higher stabilities than the corresponding chlorophosphates, allow phosphonylation of a variety of N-, O-, and S-nucleophiles in good yields.
