73622-08-9Relevant academic research and scientific papers
Phosphine boranes as less hydrophobic building blocks than alkanes and silanes: Structure-property relationship and estrogen-receptor-modulating potency of 4-phosphinophenol derivatives
Fujii, Shinya,Hashimoto, Yuichi,Matsumoto, Yuichiro,Saito, Hiroki
, (2020)
Increasing structural options in medicinal chemistry is important for the development of novel and distinctive drug candidates. In this study, we focused on phosphorus-containing functionalities. We designed and synthesized a series of phosphinophenol der
Catalyzing pyramidal inversion: Configurational lability of P-stereogenic phosphines via single electron oxidation
Reichl, Kyle D.,Ess, Daniel H.,Radosevich, Alexander T.
supporting information, p. 9354 - 9357 (2013/07/25)
We report that pyramidal inversion of trivalent phosphines may be catalyzed by single electron oxidation. Specifically, a series of P-stereogenic (aryl)methylphenyl phosphines are shown to undergo rapid racemization at ambient temperature when exposed to catalytic quantities of a single electron oxidant in solution. Under these conditions, transient phosphoniumyl radical cations (R3P?+) are formed, and computational models indicate that the pyramidal inversion barriers for these open-shell intermediates are on the order of ～5 kcal/mol. The observed 1020-fold rate enhancement over uncatalyzed pyramidal inversion opens new opportunities for the dynamic stereochemistry of phosphines and may hold additional implications for the configurational stability of P-stereogenic phosphine ligands on high-valent oxidizing transition metals.
