13410-61-2Relevant articles and documents
A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics
Taylor, Nicholas P.,Gonzalez, Jorge A.,Nichol, Gary S.,García-Domínguez, Andrés,Leach, Andrew G.,Lloyd-Jones, Guy C.
supporting information, p. 721 - 729 (2022/01/04)
The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.
Novel phosphinite and phosphonite copper(I) complexes: Efficient catalysts for click azide-alkyne cycloaddition reactions
Lal, Steven,McNally, Jayne,White, Andrew J. P.,Diez-Gonzalez, Silvia
scheme or table, p. 6225 - 6232 (2012/01/12)
The preparation of novel phosphinite- and phosphonite-bearing copper(I) complexes of the general formula [CuX(L)] is reported. These compounds, which remain scarce in the literature, could be prepared using readily available starting materials and were spectroscopically and structurally characterized. These complexes, together with their known phosphine and phosphite analogues, were then applied to the 1,3-dipolar cycloaddition of azides and alkynes, to find that the new complexes displayed the best activities. Full optimization of the reaction conditions resulted in a noteworthy Click catalytic system, active under very mild reaction conditions in the absence of any additive and using low metal loadings.
Conversion of alcohols to alkyl aryl sulfides by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite
Kuroda, Kiichi,Maruyama, Yuji,Hayashi, Yujiro,Mukaiyama, Teruaki
experimental part, p. 381 - 392 (2009/06/28)
Preparation of alkyl aryl sulfides from alcohols and arenethiols such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite (PhOPPh 2) and benzoquinone derivatives or azide compounds. This reaction proceeds under mild and neutral conditions and is applicable to the thioetherification of various alcohols in which the chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configuration.