1101-76-4Relevant academic research and scientific papers
Experiment and Theory of Bimetallic Pd-Catalyzed α-Arylation and Annulation for Naphthalene Synthesis
Ence, Chloe C.,Ess, Daniel H.,Gassaway, Kyle J.,Himes, Samuel R.,Larsen, Samantha G.,Martinez, Erin E.,Matu, Manase F.,Michaelis, David J.,Moreno, Mariur Rodriguez,Nazari, S. Hadi,Smith, Stacey J.,Valdivia-Berroeta, Gabriel A.
, p. 10394 - 10404 (2021)
We report the synthesis of bimetallic Pd(I) and Pd(II) complexes with bidentate 2-phosphinoimidazole ligands and their catalytic activity to generate substituted naphthalenes. This process involves the coupling of an aryl iodide and 2 equiv of a ketone via sequential ketone α-arylation and then annulation to generate disubstituted and tetrasubstituted naphthalenes in a regioselective manner. Excellent substrate scope for both aryl iodide and ketone partners is demonstrated, including that for heteroaryl iodides. Bimetallic Pd complexes are much more reactive than monometallic Pd catalysts in this transformation. Density functional theory calculations, isotope effect experiments, and substrate competition experiments were used to examine bimetallic mechanisms, reactivity, and selectivity.
Ligand-Free and Solvent-Free Synthesis of 1,3-Disubstituted Naphthalenes through Stille Coupling
Mkpenie, Victor,Rohand, Taoufik,Sbi, Sanae,Tanemura, Kiyoshi
supporting information, p. 903 - 906 (2020/05/28)
A variety of 1,3-disubstituted naphthalenes have been prepared by palladium-catalyzed annulation of (o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stille coupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C-C bond coupling.
