335259-42-2Relevant articles and documents
Chiral bidentate bis(N-heterocyclic carbene)-based palladium complexes bearing carboxylate ligands: Highly effective catalysts for the enantioselective conjugate addition of arylboronic acids to cyclic enones
Zhang, Tao,Shi, Min
, p. 3759 - 3764 (2008)
Axially chiral cis-chelated bidentate bis(N-heterocyclic carbene)-palladium(II) complexes with two weakly coordinating carboxylate ligands are effective catalysts for the asymmetric conjugate addition of arylboronic acids to cyclic enones, producing the corresponding adducts in moderate-to-high yields and with good-to-high enantioselectivities, in most cases under mild conditions.
Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions
Bieliūnas, Vidmantas,Ston?ius, Sigitas
, p. 3815 - 3823 (2021/07/28)
Design and synthesis of the second generation C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation of cyclic enones with arylboronic acids, providing the corresponding 1,4-addition products in good to excellent yields (69–99 %) and enantioselectivities up to 99 % ee.
Palladium-catalyzed redox cascade for direct β-arylation of ketones
Huang, Zhongxing,Dong, Guangbin
supporting information, p. 3253 - 3265 (2018/05/04)
Herein we report a full article about the detailed design and development of two palladium-catalyzed redox cascade methods that enable direct β-arylation of ketones. Palladium-catalyzed ketone dehydrogenation, aryl-X bond activation and conjugate addition were merged into a redox-neutral catalytic cycle. Non-metal-based aryl electrophiles were used as both the oxidant and the aryl source. The β-arylation with aryl iodides was achieved site-selectively with Pd(TFA)2/P(i-Pr)3 as the precatalyst and AgTFA as the iodide scavenger. Both cyclic and linear ketones can react to give β-aryl ketones with excellent functional group tolerance. The β-arylation with diaryliodonium salts was realized without stoichiometric heavy metal additives, and proved to be redox-neutral. A wider substrate scope regarding aryl groups and ketones was obtained for the arylation with diaryliodonium salts, and the possible involvement of palladium nanoparticles as the active catalyst was examined and discussed.