title: Development of efficient catalytic arylation of aldehydes with thioether-imidazolinium carbene ligands.
abstract: Effective methods of ligand design have been highly sought due to the significant roles of ligands in controlling metal catalyses. In particular, easy-to-handle ligands to realize high reaction efficacy, substrate tolerance, and environmental friendliness are desirable. Novel bidentate ligands containing N-heterocyclic carbene and thioether moieties were developed based on findings of hemilabile coordination, whose precursors were crystalline solids stable enough to handle and store in the air. The thioether-imidazolinium carbene ligand successfully brought out high catalyst performance of palladium in the catalytic arylation of aldehydes with organoboron reagents, which tolerated a diverse range of substrates including poorly reactive, sterically hindered, and heterocyclic compounds. This process was applied to gram-scale synthesis using only water as solvent with high efficiency and also achieved the effective one-pot synthesis of 3-arylphthalides known as useful biologically active agents and important synthetic intermediates for naturally occurring compounds.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University. 1–14 Bunkyo-machi, Nagasaki, Japan. mkuriyam@nagasaki-u.ac.jp
authors.forename: Masami
authors.initials: M
authors.lastname: Kuriyama
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013440:Sulfides / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D001896:Boron Compounds; D006571:Heterocyclic Compounds; D007093:Imidazoles; D008024:Ligands; D013440:Sulfides; C030011:carbene; D010165:Palladium; C029899:imidazole; D008697:Methane