Development of efficient catalytic arylation of aldehydes with thioether-imidazolinium carbene ligands.
Chem Pharm Bull (Tokyo)
; 60(4): 419-28, 2012.
Article
em En
| MEDLINE
| ID: mdl-22466724
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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Sulfetos
/
Aldeídos
/
Imidazóis
/
Metano
Idioma:
En
Revista:
Chem Pharm Bull (Tokyo)
Ano de publicação:
2012
Tipo de documento:
Article
País de afiliação:
Japão