《Reactivity and Selectivity Controlling Factors in the Pd/Dialkylbiarylphosphine-Catalyzed C-C Cleavage/Cross-Coupling of an N-Fused Bicyclo α-Hydroxy-β-Lactam》 was written by Xu, Li-Ping; Roque, Jose B.; Sarpong, Richmond; Musaev, Djamaladdin G.. Related Products of 51364-51-3 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:
D. functional theory was employed in order to elucidate the mechanism and factors that lead to the observed regioselectivity in the dialkylbiarylphosphine (Phos)/Pd-catalyzed C-C cleavage/cross-coupling of an N-fused bicyclo α-hydroxy-β-lactam, 1. We have identified that (a) a complex [(1)(Cs2CO3)]-PdL(PhBr) forms prior to a “”base-mediated oxidative addition””; (b) Cs-carbonate (rather than a halide) deprotonates the alc. substrate in the lowest energy pathway en route to Pd-alcoholate formation; (c) reactions using Phos ligands bearing OCF3 and OCF2H substituents on the “”B””-ring are predicted to be selective toward proximal ring opening of 1; (d) steric repulsion between the bottom “”B””-ring of the Phos ligand and the piperidine moiety of 1 controls the regioselectivity of the C-C cleavage followed by cross-coupling; and (e) the α- vs β-selective functionalization of the piperidine moiety in 1 is influenced by the bulkiness of the R2-substituent of the coupling partner. These studies will aid in the design of selective functionalizations of the piperidine moiety in 1. The experimental part of the paper was very detailed, including the reaction process of Tris(dibenzylideneacetone)dipalladium(0)(cas: 51364-51-3Related Products of 51364-51-3)
Tris(dibenzylideneacetone)dipalladium(0)(cas: 51364-51-3) is used in the preparation of semiconducting polymers processed from nonchlorinated solvents into high performance thin film transistors.Related Products of 51364-51-3It is used as catalyst for the synthesis of epoxides, alpha-arylation of ketones, in combination with BINAP for the asymmetric heck arylation of olefins, site-selective benzylic sp3 palladium-catalyzed direct arylation and homoallylic diamination of terminal olefins.
Referemce:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI