Electric Literature of 1038-95-5. Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. Like 1038-95-5, Name is Tri-p-tolylphosphine. In a document type is Article, introducing its new discovery.
(Figure presented) Silver(I) complex [Ag(diene)2] +Y- (where diene = cyclooctadiene, norbornadiene, and 1,3-cyclohexadiene; Y- = PF6-, BF 4-) efficiently catalyzes the arylation of N-tosylaziridines with arenes and heteroarenes under ambient condition to provide the corresponding beta-aryl amine derivatives with excellent regioselectivity. To understand the nature of substrate activation, and initial bond breaking/making steps, the following studies were conducted with the help of in situ NMR (1H, 31P, 109Ag) and ESI-MS probe: (I) evaluation of Hammett reaction constant (-); (II) correlation of initial rate (k) versus cone angle (theta) of ligand L for reactions mediated by [Ag(COD)2]PF6/L (where L is a phosphine or a phosphite ligand); (III) identification of silver-arene intermediates in solution; and (IV) correlation of initial rate (k) with deltaHOMO-LUMO of [Ag(diene)2]PF6 obtained from preliminary DFT studies. Study I led to a p-value of -0.586, indicating that the extent of electrophilic perturbation is considerably less than a typical Lewis acid catalyzed process. Study II indicated that initial rate (k) increases with concomitant increase in theta, as well with delta31P(complex-ligand), which corroborates to a mechanism involving prior ligand dissociation. Study III showed the plausible formation of [Ag(diene)(arene)]+ and [Ag(arene)2]+ as reactive species in solution. Study IV showed that the dependence of initial rate (k) with diene ligand is in the order COD > NBD > CHD; which corresponds well with the order of hardness of the respective Ag(I) complexes.
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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate